cas 808758-81-8, 4-(bis(4-iodophenyl)aMino)benzaldehyde

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Improving device performance of p-type organic field-effect transistor using butterfly like triarylamines
Facile and economic strategy to create a controlled self-structured architecture of semiconducting molecules is very crucial in the accomplishment of carbon electronic devices. A series of new unsymmetrically functionalized butterfly type triarylamines with electron donating/withdrawing substituents were synthesized. Simple and efficient solution based method was used as a successful strategy for OFET with improved characteristics. Binary solvent system with chloroform and toluene (7:3) has improved inter/intra molecular communication in the active layer. The morphology of the films was analyzed by SEM reveals the uniform packing. In addition post thermal annealing has enhanced the crystallinity with minimal grain boundaries. HOMO values -5.1 to -5.4 eV obtained from cyclic voltammetry ensure that these molecules can efficiently transport holes. OFET devices were fabricated in bottom gate top contact (BGTC) architecture by spin coating. Molecules exhibited typical p-channel transistor behavior with mobility up to 1 cm2 V?1s?1 with 106 Ion/off current ratio. Density functional theory (DFT) visualized the packing and interaction of molecules and supported the efficient mobility. Our investigation gives insight into the role of solvents to control the film architecture in solution processing OFET device construction.
Dheepika, Ramachandran,Shaji, Anisha,Imran, Predhanekar Mohamed,Nagarajan, Samuthira
(2020)
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Temperature effect on the optical properties of two different triphenylamine-based organic dyes
In this paper, we present the absorption and photoluminescence (PL) spectra of conjugated, metal-free organic dyes, triphenylamine derivatives 3-(4-(bis(4-(5-(4-(hexyloxy)phenyl)thiophenyl)phenyl)amino)phenyl)-2-cyanoacrylic acid (OD3) and (E)-3-(5′-(4-(bis(4-(5-(4-hexyloxy)phenyl)thiophen-2-yl)phenyl)amino)phenyl)-2,2′-bithiophen-5-yl)-2-cyanoacrylic acid (OD3DT), with and without a π-conjugated bridge, respectively, in film at a temperature range from 13 to 400?K. We find that the intensities of absorption and PL of OD3 decrease gradually beyond 200?K, as well as the ratios of integral areas of absorption to PL spectra. However, the other compound, OD3DT, shows a very different behavior. An increase is discovered in the ratio of the absorption to PL integral area when the temperature is higher than 200?K. A π-conjugated bridge gives this compound a higher degree of symmetry, and therefore, a better alignment of the molecules in the film, which causes a stacking aggregation such that the temperature effect on this compound is different than OD3.
Hsu, Che-Hung,Wu, Chi-Tai,Yang, Shu-Chun,Chang, Yu-Cheng,Huang, Chih-Hong,Chang, Shu-Mei
p. 3573 - 3583
(2017)
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A novel pyridyl triphenylamine–BODIPY aldoxime: Naked-eye visible and fluorometric chemodosimeter for hypochlorite
An aldoxime containing fluorescent probe based on vinylpydine-appended triphenylamine–BODIPY has been designed and used for hypochlorite detection. OX-PPA-BODIPY was developed by introducing an aldoxime group into the 2-position of BODIPY, which can be used for the detection of hypochlorite with a sharp color change from pink to green. The attachment of 4-vinylpyridine moiety to triphenylamine–BODIPY constructs a fluorogen with desirable conjugated system. The probe, which displays extremely weak fluorescence owing to the C[dbnd]N isomerization mechanism at 2-position of BODIPY, responds to HClO/ClO? through a dramatic enhancement of its fluorescence intensity. This new probe, a naked-eye visible and fluorometric chemodosimeter, exhibits high selectivity and sensitivity toward hypochlorite over other reactive oxygen species (ROS) and anions. The detection is accompanied by a 20-fold increase in fluorescent intensity (ΦF from 0.02 to 0.43). The detection limit of the probe for hypochlorite is 7.37?×?10??7?M. Moreover, OX-PPA-BODIPY can be used to detect hypochlorite in real water samples.
Xu, Xiu-xiu,Qian, Ying
p. 356 - 361
(2017)
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An AIE dye based smartphone and LDA integrated portable, intelligent and rapid detection system as trace water indicator and cyanide detector
Portable, rapid, accurate and on-site detection of analysis target has always been the goal of continuous efforts in the field of analysis. In this work, a novel intelligent and rapid detection system based on an AIE dye (TPA-DCV) was established for portable and on-site detection of trace water in organic solvents and CN? in water by integrating the smartphone and linear discriminant analysis (LDA). The TPA-DCV displayed remarkable solvatochromism effect and showed different fluorescence colors to different water contents of different solvents, with the minimum detection limit of 54 ppm. In addition, TPA-DCV also exhibited specific response to CN?, and showed significant fluorescence changes to different amounts of CN?. With the assist of this detection system, these different fluorescence color signals could be accurately classified in canonical score plot. What's more, the classification and distribution of fluorescence color in canonical score plot showed regular change with the target concentration, which could be used to quantify the trace water and CN?. The rationality and practicability of this detection system were preliminary verified by a large number of real sample analyses. This detection system greatly simplifies the analysis process, which is in the proof of intelligent and rapid detection just using a simple color analysis without any instrument test, which may be a big step forward.
Chen, Linfeng,Tian, Xike,Li, Yong,Yang, Chao,Lu, Liqiang,Zhou, Zhaoxin,Nie, Yulun
p. 1 - 7
(2019)
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Highly selective flurogenic chemosensor for cyanide ion in aqueous medium and its applications of logic gate and Hela cells
We have successfully synthesized triphenylamine-based fluorophores (MK and HK) with cyanoacrylic acid as a receptor for CN– ion sensing in a 99% aqueous medium. From the emission titration spectra, the detection limit of cyanide ion calculated towards MK and HK, respectively, are 234 nM and 11 nM. The observed binding constants for MK and HK, respectively, are 27 × 10-3 M and 10 X 10-2 M. The plausible sensing mechanism is confirmed by various methods such as Job's plot experiment, proton NMR titration, and density functional theory. Furthermore, the prominent application is the naked-eye detection of cyanide from non-fluorescent to greenish-yellow fluorescent under 365 nm UV light. Based on the observed data from fluorescence spectroscopic studies, a new logic circuit is designed. Moreover, the potential application of HK and MK in the Hela cell line exhibited turn on fluorescence image for cyanide ion through the inhibition of the ICT process. In addition to that, the probe MK and HK is successfully applied in the analysis of the real sample for the rapid detection of cyanide ions.
Muniyasamy, Harikrishnan,Chinnadurai, Chithiraikumar,Nelson, Malini,Kubendran, Aravind Manikka,Sukumaran, Karthika,Balasubramaniem, Ashokkumar,Sepperumal, Murugesan,Ayyanar, Siva,Govindasamy, Mani,Ghfar, Ayman,Alsubaied, Fehaid Mohammed
(2021/04/23)

Acid-induced tunable white light emission based on triphenylamine derivatives
A series of triphenylamine (TPA) derivatives with various substituent groups were prepared and showed different absorption and fluorescence characteristics due to the substituent effect. On account of the existence of pyridine units, these TPA derivatives exhibited acid-induced tunable multicolor fluorescence emission including white light emission. In addition, acid-induced fluorescence regulation of these compounds has been also realized in the solid state, which enable them to be successfully constructed the stimuli-responsive fluorescent films and fluorescent inks for inkjet printing.
Liu, Xi,Qin, Yi,Zhu, Junlong,Zhao, Xiaoli,Cheng, Tanyu,Jiang, Yanrong,Sun, Haitao,Xu, Lin
supporting information
p. 1537 - 1540
(2020/11/12)

Axial-symmetric conjugated group promoting intramolecular charge transfer performances of triphenylamine sensitizers for dye-sensitized solar cells
The intramolecular charge transport (ICT) process directly determines the charge generation, transport, and even injection of the dye-sensitized solar cell (DSSC) sensitizer. Herein, we constructed a new series of D-π-A system by linking 4-methoxyphenyl and triphenylamine donors with an ethynyl group having an axial-symmetric conjugated system. Since the axisymmetric conjugate group overcomes the reduction of the conjugate characteristic caused by the plane distortion, the molecular ICT performance and the electronic recombination inhibition are effectively improved. As a result, the photoelectric conversion efficiency was increased from 3.43% to 6.37% by means of the extension of the π-bridge at same time. It provides a new idea for the design and development of DSSC sensitizers in the future.
Chen, Shaorui,Pei, Juan,Pang, Zhihan,Wu, Wenjun,Yu, Xudong,Zhang, Cong
(2019/11/28)

NARROW ABSORPTION POLYMER NANOPARTICLES AND RELATED METHODS
Polymers, monomers, narrow-band absorbing polymers, narrow-band absorbing monomers, absorbing units, polymer dots, and related methods are provided. Bright, luminescent polymer nanoparticles with narrow-band absorptions are provided. Methods for synthesizing absorbing monomers, methods for synthesizing the polymers, preparation methods for forming the polymer nanoparticles, and applications for using the polymer nanoparticles are also provided.
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(2020/04/25)

New ferrocenyl-containing organic hole-transporting materials for perovskite solar cells in regular (n-i-p) and inverted (p-i-n) architectures
Three triphenylamine derivatives containing ferrocenyl groups (JW6, JW7 and JW8) were synthesized by facile syntheses. Their HOMO levels match the valence band energy of CH3NH3PbI3. The introduction of ferrocenyl was aimed to obtain hole transporting materials with high mobility for perovskite solar cells. JW7 shows higher hole mobility (4.2 × 10?4 cm2 V?1 s?1) than JW6 (1.3 × 10?4 cm2 V?1 s?1) and JW8 (1.5 × 10?4 cm2 V?1 s?1). Their film-forming properties are affected by their molecule structures. The methoxyl and N,N-dimethyl terminal substituents of JW7 and JW8 are beneficial for having better solubility than JW6. The regular mesoporous TiO2-based perovskite solar cells (n-i-p) and the inverted planar heterojunction perovskite solar cells (p-i-n) fabricated using JW7 show the highest power conversion efficiency of 9.36% and 11.43% under 100 mW cm?2 AM1.5G solar illumination. For p-i-n cells, the standard HTM PEDOT-based cell reaches an efficiency of 12.86% under the same conditions.
Jia, Jingwen,Duan, Liangsheng,Chen, Yu,Zong, Xueping,Sun, Zhe,Wu, Quanping,Xue, Song
p. 216 - 223
(2019/01/16)

Solution-Processable Unsymmetrical Triarylamines: Towards High Mobility and ON/OFF Ratio in Bottom-Gated OFETs
Self-assembly of organic small molecules into an ordered thin film has been the key strategy towards efficient charge transport for organic field-effect transistors (OFETs). Solution processing is a feasible and economic way to enhance pi–pi interaction. Herein, nitrile-substituted unsymmetrical triarylamines for OFET applications with high mobility are reported. The compounds were constructed by Suzuki cross-coupling reactions under inert conditions. The HOMO level of about 5.3 eV indicates good hole-transporting ability. OFETs were assembled in bottom-gate, top-contact architecture. Devices fabricated from a binary solvent system exhibited excellent p-channel characteristics, with impressively high charge-carrier mobility of up to 2.58 cm2 V?1 s?1 and ION/OFF current ratios of 106–107. SEM and AFM analysis showed the efficient molecular self-assembly attained by the simple and effective solvent-engineering method. Theoretical insights obtained by DFT calculations supported by single-crystal structures showed that the crystalline nature and packing modes of these compounds ensure high mobility. The results prove that these compounds have great potential for use in numerous electronic applications, such as sensors and logic switches.
Dheepika, Ramachandran,Mohamed Imran, Predhanekar,Bhuvanesh, Nattamai S. P.,Nagarajan, Samuthira
p. 15155 - 15163
(2019/11/14)

ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELL
The present invention relates to an organic dye having improved stability to heat, light and water, to a composition comprising the same, and to a dye-sensitized solar cell and, more specifically, to an organic dye represented by chemical formula 1, to a composition comprising the same, and to a dye-sensitized solar cell. The chemical formula 1 is the same as defined in claim 1.COPYRIGHT KIPO 2020
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(2019/12/25)

Cyano three aniline organic small molecule red light material and its synthesis and use
The invention discloses a cyanotriphenylamine organic small molecular red emitting material, a synthesis method and use thereof. The synthesis method includes: taking triphenylamine as the raw material to react with POCl3 to synthesize an intermediate 4-(diphenylamino)benzaldehyde; subjecting the 4-(diphenylamino)benzaldehyde to reaction to obtain 4-bis(4-iodophenyl)aminobenzaldehyde; reacting the 4-bis(4-iodophenyl)aminobenzaldehyde with diphenylamine to obtain 4-(bis-(4-(diphenylamino)phenyl)amino)benzaldehyde and 4-((4-( diphenylamino)phenyl)(4-iodophenyl)amino)benzaldehyde; and reacting 4-(diphenylamino)benzaldehyde and the product of the last step respectively with malononitrile, cyano-acrylate or 2-(3, 5, 5-trimethylcyclohexenyl-2-octenylidene)malononitrile to obtain a novel cyanotriphenylamine compound. The invention preliminarily studies the relevant optical properties of the product, and lays the foundation for development of the product into a novel red emitting material with excellent performance.
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(2018/05/16)

Carbazole functionalized new bipolar ligand for monochromatic red light-emitting europium(iii) complex: combined experimental and theoretical study
A carbazole functionalized novel class of bipolar ligand and their corresponding β-diketonate Eu(iii) complex was designed, synthesized and characterized successfully. The photoluminescence results show that the efficient energy transfer occurs from the ligand to the europium(iii) center metal ion, and a narrow band red emission with apt CIE color gamut is observed. TD-DFT calculations were performed to know the energies of the singlet (1S) and triplet (3T) levels for the bipolar ligand and good overlap between the ligand triplet level and Eu(iii) excited level is shown. The PL quantum yield was found to be 44.4%, and the lifetime of the complex was investigated, which is found to be 0.53 ms in chloroform solution. HOMO and LUMO energy level energies (redox reaction) were calculated from the electrochemical analysis for the Eu(iii)-complex, and the values were 5.7 and 3.0 eV, respectively. The synthesized Eu(iii) complex was doped with polymethylmethacrylate in different percentage ratios, and it was found that the concentration variation influenced on intensity as well as symmetry. The complex is stable up to 270 °C as observed from differential scanning calorimetry-thermogravimetric analysis, which signifies that it is a promising candidate for further investigations.
Rajamouli,Dwaraka Viswanath,Giri,Jayasankar,Sivakumar
p. 3112 - 3123
(2017/04/14)

Controlled Energy Transfer from a Ligand to an EuIII Ion: A Unique Strategy to Obtain Bright-White-Light Emission and Its Versatile Applications
A new diphenylamine-functionalized ancillary-ligand-coordinated europium(III) β-diketonate complex showed incomplete photoexcitation energy transfer from a ligand to a EuIII ion. A solvatochromism study led to a balancing of the primary colors to obtain single-molecule white-light emission. Thermal-sensing analysis of the europium complex was executed. The europium complex, conjugated with a near-UV-light-emitting diode (395 nm), showed appropriate white-light-emission CIE color coordinates (x = 0.34 and y = 0.33) with a 5152 K correlated color temperature.
Boddula, Rajamouli,Singh, Kasturi,Giri, Santanab,Vaidyanathan, Sivakumar
p. 10127 - 10130
(2017/09/12)

D - D - π - A - type indole - triphenylamine the solar-sensitizing dye and its synthesis and use
The invention discloses an indole-triphenylamine-arylmethylidenemalononitrile solar energy co-sensitization dye, a synthetic method and application thereof. The synthetic method comprises the following steps: adopting triphenylamine as the raw material, carrying out reaction on triphenylamine and POCl3 in a DMF solvent to compound and obtain an intermediate 4-(diphenyl amido) benzaldehyde; carrying out reaction on the 4-(diphenyl amido) benzaldehyde to obtain 4-bis (4-iodophenyl) aminobenzaldehyde; respectively carrying out reaction on the 4-bis (4-iodophenyl) aminobenzaldehyde and indole, 2-methylindole and 3-methylindole to obtain an indole-triphenylamine aldehyde derivative; respectively carrying out reaction on the indole-triphenylamine aldehyde derivative and cyanoacetic acid, malononitrile or 2-(3, 5, 5-trimethyl cyclohexene-2-octenylidene) malononitrile to obtain an indole-arylmethylidenemalononitrile-triphenylamine derivative. According to the synthetic method, the relevant optical property, photo-electro transition rate and co-sensitization efficiency of the product are primarily studied, and the foundation for developing the dye into a novel solar energy co-sensitization dye with excellent properties is laid.
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(2017/10/11)

Fluorophore-functionalized graphene oxide with application in cell imaging
In this work, we fabricated a novel triphenylamine-derivative (DNDT)-modified nanographene oxide by following a simple gram-scale method. The product showed interesting optical properties and good potential for use in bioimaging applications. This fluorescent carbon material could be readily internalized by HepG2 cells and was clearly visualized to accumulate mainly in the nucleus.
Lei, Lei,Ma, Hengchang,Yang, Manyi,Qin, Yanfang,Ma, Yucheng,Wang, Tao,Yang, Yuan,Lei, Ziqiang,Lu, Dedai,Guan, Xiaolin
p. 12375 - 12379
(2017/11/06)

Molecular Engineering of UV/Vis Light-Emitting Diode (LED)-Sensitive Donor–π–Acceptor-Type Sulfonium Salt Photoacid Generators: Design, Synthesis, and Study of Photochemical and Photophysical Properties
A series of donor–π–acceptor-type sulfonium salt photoacid generators (PAGs) were designed and synthesized by systematically changing electron-donating groups, π-conjugated systems, electron-withdrawing groups, and the number of branches through molecular engineering. These PAGs can effectively decompose under UV/Vis irradiation from a light-emitting diode (LED) light source because of the matching absorption and emitting spectra of the LEDs. The absorption and acid-generation properties of these sulfonium salts were elucidated by UV/Vis spectroscopy and so forth. Results indicated that the PAG performance benefited from the introduction of strong electron-donating groups, specific π-conjugated structures, certain electron-withdrawing groups, or two-branched structures. Most sulfonium salts showed potential as photoinitiators under irradiation by a wide variety of UV and visible LEDs.
Wu, Xingyu,Jin, Ming,Xie, Jianchao,Malval, Jean-Pierre,Wan, Decheng
supporting information
p. 15783 - 15789
(2017/10/20)

Novel green-yellow-orange-red light emitting donor-π-acceptor type dyes based on 1,3-indandione and dimedone moieties
Ten novel luminescent dyes containing 1,3-indandione or dimedone as electron acceptors, amino derivatives (dimethylamino, diphenylamino, julolidine and dibiphenylamino) as electron donor units and different length olefinic linkers (1-hydroxyallylidene or 1-hydroxypenta-2,4-dien-1-ylidene) are reported in this study. Newly synthesized compound structures are proven with X-ray analysis, 1H, 13C NMR spectroscopy and elemental analysis. The UV–Vis absorption, emission, solvatochromism, solvatofluorochromism, redox properties, as well as thermal stabilities and quantum chemical calculations of these dyes were systematically investigated to outline relation between structure and properties. These dyes exhibit moderate thermal decomposition temperatures above 200?°C, insignificant solvatochromism and positive, significant solvatofluorochromism, large Stokes shifts and green, yellow, orange and red light emission with quantum yields in range from 0.03 to 0.93 in non-polar solvents and in thin films. Quantum-chemical calculations (DFT) shows, that all dyes exhibit small HOMO/LUMO gaps from 2.77 to 3.22?eV, which is in agreement with experimental data.
Malina, Ilze,Kampars, Valdis,Turovska, Baiba,Belyakov, Sergey
p. 820 - 830
(2017/01/21)

Synthesis, Electrochemistry, and Photophysical Studies of Ruthenium(II) Polypyridine Complexes with D–π–A–π–D Type Ligands and Their Application Studies as Organic Memories
A new class of ruthenium(II) polypyridine complexes with a series of D–π–A–π–D type (D=donor, A=acceptor) ligands was synthesized and characterized by1H NMR spectroscopy, mass spectrometry, and elemental analysis. The photophysical and electrochemical properties of the complexes were also investigated. The newly synthesized ruthenium(II) polypyridine complexes were found to exhibit two intense absorption bands at both high-energy (λ=333–369 nm) and low-energy (λ=520–535 nm) regions. They are assigned as intraligand (IL) π→π* transitions of the bipyridine (bpy) and π-conjugated bpy ligands, and IL charge-transfer (CT) transitions from the donor to the acceptor moiety with mixing of dπ(RuII)→π*(bpy) and dπ(RuII)→π*(L) MLCT characters, respectively. In addition, all complexes were demonstrated to exhibit intense red emissions at approximately λ=727–744 nm in degassed dichloromethane at 298 K or in n-butyronitrile glass at 77 K. Nanosecond transient absorption (TA) spectroscopy has also been carried out, establishing the presence of the charge-separated state. In order to understand the electrochemical properties of the complexes, cyclic voltammetry has also been performed. Two quasi-reversible oxidation couples and three quasi-reversible reduction couples were observed. One of the ruthenium(II) complexes has been utilized in the fabrication of memory devices, in which an ON/OFF current ratio of over 104was obtained.
Leung, Ming-Yi,Leung, Sammual Yu-Lut,Wu, Di,Yu, Tao,Yam, Vivian Wing-Wah
p. 14013 - 14021
(2016/09/21)

Water-Soluble Fluorescent Probes for Selective Recognition of Lysine and Its Application in an Object Carry-and-Release System
A water-soluble fluorescent probe PEG-TPA-5′ was synthesized, which shows an excellent selectivity to detect Lys in aqueous phase. An object carry-and-release system is established by applying PEG-TPA-5′ as carrier and Lys as chemical stimulating source.
Ma, Hengchang,Qi, Chunxuan,Cao, Haiying,Zhang, Zhongwei,Yang, Zengming,Zhang, Bing,Chen, Chao,Lei, Zi Qiang
supporting information
p. 58 - 63
(2016/01/16)

Triphenylamine-based π-conjugated dendrimers: Convenient synthesis, easy solution processability, and good hole-transporting properties
Two, third-generation triphenylamine-based dendrimers (DT1 and DT2) were prepared through a simple convergent approach by using a combination of versatile carbon-carbon formation reactions. It is found that the π-linkages connecting the periphery into the core have a pronounced effect on the properties of the material. The introduction of CC bonds in the periphery improves the photophysical behavior and optical qualities of the films in comparison with their introduction in the core of the dendrimer. Both dendrimers exhibit high Tgs (above 240 °C) and high-lying HOMO energy levels of ～5.2 eV. As the hole-transporting layer fabricated through a facile solution process, DT2 can endow an Alq3 based multi-layer OLED device with a maximum brightness of 5020 cd m-2, and a maximum current efficiency of 2.36 cd A-1.
Li, Zhong'An,Ye, Tenglin,Tang, Sun,Wang, Can,Ma, Dongge,Li, Zhen
p. 2016 - 2023
(2015/04/27)

Enhanced electro-optic activity from the triarylaminophenyl-based chromophores by introducing heteroatoms to the donor
A series of chromophores T1-T3 based on the same thiophene π-conjugation and tricyanofuran acceptor (TCF) but with different heteroatoms in the triarylaminophenyl (TAA) donors have been synthesized and systematically investigated in this study. Density functional theory (DFT) was used to calculate the HOMO-LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. Moreover, to determine the redox properties of these chromophores, cyclic voltammetry (CV) experiments were performed. After introducing the heteroatom to the benzene ring of the TAA donor, reduced energy gaps of 1.28 and 0.84 eV were obtained for chromophores T2 and T3, respectively, which was much lower than for chromophore T1 (ΔE = 1.46 eV). These chromophores showed excellent thermal stability with their decomposition temperatures all above 280 °C. Compared with results obtained from the chromophore without the heteroatom (T1), these new chromophores show better intramolecular charge-transfer (ICT) absorption. Most importantly, the high molecular hyperpolarizability (β) of these chromophores can be effectively translated into large electro-optic (EO) coefficients (r33) in the poled polymers. The electro-optic coefficient of poled films containing 25 wt% of these new chromophores doped in amorphous polycarbonate (APC) afforded values of 16, 58 and 95 pm V-1 at 1310 nm for chromophores T1-T3, respectively. High r33 values indicated that introducing heteroatom to the benzene ring of the TAA donor can efficiently improve the electron-donating ability, which improves the hyperpolarizability (β). The long-chain on the benzene ring of the TAA donor, acting as the isolation group, may reduce intermolecular electrostatic interactions, thus enhancing the macroscopic EO activity. These properties, together with the good solubility, suggest the potential use of these new chromophores as advanced material devices. This journal is
Yang, Yuhui,Liu, Fenggang,Wang, Haoran,Bo, Shuhui,Liu, Jialei,Qiu, Ling,Zhen, Zhen,Liu, Xinhou
p. 5297 - 5306
(2015/05/27)

Triphenylamine-decorated BODIPY fluorescent probe for trace detection of picric acid
Triphenylamine-decorated BODIPY derivative TBMA was designed and synthesized. Luminogen aggregation was developed by taking advantage of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) processes. In non-polar solvents, the locally excited (LE) states of BODIPY luminogens emitted intense yellow light. Increasing solvent polarity brought the luminogens from an LE to a TICT state, causing a large bathochromic shift in the emission color and a dramatic decrease in emission efficiency. The red emission was greatly boosted by aggregate formation or AIE effect. We also discovered that TBMA could be applied as an efficient chemical sensor for picric acid (PA) detection. The detection limit and quenching constant (KSV) were determined as 30 ppb and 2.1 × 10-6 M-1 respectively. 19F NMR and 1H NMR titration analysis verified that F...H hydrogen bonding is demonstrated as the mode of interaction, which possibly facilitates effective exciton migration.
Hengchang, Ma,Zhongwei, Zhang,Yuanyuan, Jin,Lajia, Zha,Chunxuan, Qi,Haiying, Cao,Zengming, Yang,Zhiwang, Yang,Ziqiang, Lei
p. 87157 - 87167
(2015/11/17)

A novel triphenylamine-based dye sensitizer supported on titania nanoparticles and the effect of titania fabrication on its optical properties
A new synthesised triphenylamine-based dye having a branched structure with one OH-ending branch able to interact with the surface hydroxyl moieties of mesoporous TiO2 is reported. Optical properties of the dye-titania hybrid material are presented and the higher efficiency of the dye on pure anatase TiO2 compared to the commercial Degussa P25, which contains a rutile phase component, is confirmed. The optical and chemical properties of the dye make it a promising candidate as a metal-free dye for DSSCs or as a host for a variety of transition or main group metal ions for different applications.
Moretti, Elisa,Aversa, Manuela,Scrivanti, Alberto,Storaro, Loretta,Talon, Aldo,Marin, Riccardo,Cecilia, Juan Antonio,Rodríguez-Castellón, Enrique,Polizzi, Stefano
p. 218 - 230
(2015/11/23)

High IPCE performance of photosensitized dyes having trifluoromethylacrylic acid as an acceptor-anchor moiety
Novel photosensitized dyes having trifluoromethylacrylic acid as an acceptor-anchor moiety (MCL2629) are synthesized. These dyes seem to suppress the back-donation currents from the conduction band of TiO2 semiconductor to the electrolyte. Their fabricated dye-sensitized solar cells (DSCs) show high IPCE performances (MCL27; over 80% between 400520 nm, max 90% at 465 nm). In particular, the high IPCE properties are compared with more than 80 article examples.
Iwata, Satoru,Oshio, Shouta,Kobayashi, Shintaro,Aoyama, Misa,Tanaka, Kiyoshi
supporting information
p. 1398 - 1400
(2015/11/24)

Carbazole-functionalized organic photosensitizer for dye-sensitized solar cells
We designed and synthesized the photosensitive ?? -conjugated organic dyes (CB-1, CB-2 and CB-3) with the carbazole substituted triphenylamine moiety as an electron donor unit and the cyanoacetic acid moiety as an acceptor for the application as a photosensitizer of dye-sensitized solar cells. The dyes with two carbazole units connected to triphenylamine moiety (CB-2 and CB-3) showed enhanced electron donating property than the one with one carbazole moiety as an electron donor unit (CB-1), which resulted in longer absorption maximum wavelength, higher overall photon to current conversion efficiency and IPCE values. In particular, CB-3 showed an absorption maximum wavelength at 428 nm and overall solar-to-energy conversion efficiency of 7.58% at AM 1.5 illumination (100 mW.cm-2) without mask.
Lee, Jeonghun,Im, Hunbae,Kim, Sukwon,Kim, Chulhee
p. 1434 - 1442
(2015/02/19)

Self-host homoleptic green iridium dendrimers based on diphenylamine dendrons for highly efficient single-layer PhOLEDs
The fabrication of electroluminescent devices that combine high device performance with simple device configuration remains an attractive challenge due to their low cost and simple fabrication processes. In this paper, a new series of electrophosphorescent small molecule iridium(iii) complexes with diphenylamine-based dendrons of good solubility have been designed. The relationships between their dendritic structures and their photophysical, electrochemical, and electrophosphorescent performances have been systematically investigated. With second-generation dendrons, the photoluminescence quantum yields of the neat film of the dendrimers are almost seven times higher than that of their prototype G0 (Ir(LG0)3, LG0 = 1-methyl-2-phenyl-1H- benzimidazole), and three times that of the first-generation dendron G1 (Ir(LG1)3, LG1 = 4-(1-methyl-1H-benzimidazol-2-yl)-N,N- diphenylbenzenamine). High-quality films of the dendrimers G2 (Ir(LG2) 3, LG2 = 1-methyl-2-[4-bis[4-(diphenylamino)phenyl]-aminophenyl]-1H- benzimidazole) and G2Cz (Ir(LG2Cz)3, LG2Cz = 1-methyl-2-[4-bis[4-(9- carbazolyl)phenyl]-aminophenyl]-1H-benzimidazole) have been fabricated by spin-coating, producing highly efficient, non-doped phosphorescent organic light-emitting diodes (PhOLEDs). With a device structure of indium tin oxide/poly(3,4-ethylene-dioxythiophene):poly(styrene sulfonic acid)/neat dendrimer/Cs2CO3/Al, maximum luminous efficiencies of 14.02 cd A-1 and 18.35 cd A-1 have been realized, exhibiting ultrahigh luminous efficiency for single-layer self-host green PhOLEDs. The excellent performances are due to the flower bouquet-shaped iridium dendrimers, which may improve the electron injection and result in greater balance between electron and hole fluxes by the exposure of electron-deficient moieties. The molecular design reported here provides a simple and effective approach to balance charge injection/transporting capacities and develops highly efficient non-doped phosphors suitable for low-cost single-layer device technologies.
Tian, Wenwen,Yi, Chang,Song, Bo,Qi, Qi,Jiang, Wei,Zheng, Yingping,Qi, Zhengjian,Sun, Yueming
p. 1104 - 1115
(2014/02/14)

Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives
The study of the chemical and electrochemical fluorescence switching properties of a family of substituted triphenylamine derivatives is reported. First of all, the synthesis of a family of six compounds is described. They are characterized by electrochemistry, UV-vis and fluorescence spectroscopy and spectroelectrochemistry. Theoretical calculations were performed in order to corroborate the experimental results. While these compounds emit blue to green light under UV irradiation with a large quantum yield (37%) in the case of one molecule, the fluorescence intensity is quenched upon oxidation. The fluorescence behavior can be switched between the strong fluorescent (neutral) state and the non-fluorescent (oxidized) state with a high contrast (around 1500 for the fluorescence intensity for one of these molecules). Furthermore, the chromatic contrast of three of these molecules reaches 70% that can be important for further applications. This journal is the Partner Organisations 2014.
Quinton, Cassandre,Alain-Rizzo, Valerie,Dumas-Verdes, Cecile,Miomandre, Fabien,Clavier, Gilles,Audebert, Pierre
p. 34332 - 34342
(2014/12/09)

Ferrocenyl substituted triphenylamine based donor-acceptor molecular systems; Synthesis, photophysical, electrochemical, and theoretical studies
A series of push-pull molecular systems 5-14 were designed, and synthesized by the Sonogashira cross-coupling, Knoevenagel condensation, and cycloaddition reactions. The donor 'ferrocenyl substituted triphenylamine' was kept constant, whereas the acceptors were varied (malononitrile, indanone, and tetralone). The electronic absorption spectra of the ferrocenyl substituted triphenylamine based donor-acceptor (D-A) compounds 5-9 exhibit intense intramolecular charge transfer (ICT) band in the visible region (415-502 nm). The incorporation of the tetracyanoethylene (TCNE) group in compounds 5-9 results in new D-A system 10-14, which exhibits the ICT band in the region 630-700 nm. The electrochemical studies suggest considerable donor-acceptor interaction. The computational studies reveal strong D-A interaction, and show good agreement with the experimental results.
Maragani, Ramesh,Misra, Rajneesh
p. 3390 - 3399
(2014/05/06)

Alkyl-triphenylamine end-capped triazines with AIE and large two-photon absorption cross-sections for bioimaging
In the present study, three new luminogens ATT-(1-3) based on 1,3,5-triazine and end-capped with multi-branched triphenylamine-containing alkyl chains have been synthesized and characterized. All the three dyes are nonemissive in solution but have a strong red fluorescent emission in the aggregate state. The two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique are determined to be as large as 2756, 4750 and 10003 GM for ATT-1, ATT-2 and ATT-3 in chloroform, respectively, showing a dramatic enhancement with an increasing number of donor branches. The relationship between their structures and properties on one- and two-photon absorption and aggregation-induced emission (AIE) is discussed, which can serve as a guideline for the development of a series of solid materials with larger two-photon cross sections and high fluorescence quantum yield. In addition, one- and two-photon fluorescence (2PF) microscopy images of HeLa cells incubated with these three dyes were obtained to demonstrate the potential applications of these fluorophores in biosensing and bioimaging.
Gao, Yuting,Qu, Yi,Jiang, Tao,Zhang, Hao,He, Nannan,Li, Bo,Wu, Junchen,Hua, Jianli
p. 6353 - 6361
(2014/08/05)

A red fluorescent 'turn-on' chemosensor for Hg2+ based on triphenylamine-triazines derivatives with aggregation-induced emission characteristics
A new sensitive and selective red fluorescence 'turn on' chemosensor 1 for Hg2+ was developed by taking advantage of AIE feature of triphenylamine-triazines motif and the specific binding of thymine with Hg 2+. Moreover, chemosensor 1 exhibited large two-photon absorption cross-section (3328 GM).
Zhang, Hao,Qu, Yi,Gao, Yuting,Hua, Jianli,Li, Jing,Li, Bo
supporting information
p. 909 - 912
(2013/03/13)

Synthesis, Two-photon absorption and AIE properties of multibranched thiophene-based triphenylamine derivatives with triazine core
Two new multibranched thiophene-based triarylamine derivatives with 1,3,5-triazine core are synthesized and characterized. Their one- and two-photon absorption properties and aggregation-induced emission effect have been investigated. Both the STAPA-based compounds are AIE active. The two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique are determined to be 620 and 1610 GM for STAPA-a and STAPA-b in chloroform, respectively, which dramatically increase with the introduction of alkyl chains. The relationship between their structures and properties on one- and two-photon absorption and aggregation-induced emission is discussed, which allows us to examine the effect of introducing alkyl chains. In addition, solvent effects also show a significant influence on the 2PA cross section. The two compounds with excellent AIE and 2PA properties provide attractive alternatives for the biophotonic materials.
Gao, Yuting,Zhang, Hao,Jiang, Tao,Yang, Ji,Li, Bo,Li, Zhen,Hua, Jianli
p. 1204 - 1212
(2013/09/23)

New thermally stable piezofluorochromic aggregation-induced emission compounds
New piezofluorochromic compounds with high thermal stabilities and aggregation-induced emission behavior were developed. The spectroscopic properties and morphological structures of these compounds were reversed upon pressing (or grinding)/annealing (or fuming). The switchable color change feature and aggregation-induced emission make the compounds promising candidates for optical recording, pressure-sensing, and light-emitting systems.
Li, Haiyin,Zhang, Xiqi,Chi, Zhenguo,Xu, Bingjia,Zhou, Wei,Liu, Siwei,Zhang, Yi,Xu, Jiarui
p. 556 - 559
(2011/04/23)

The synthesis and photophysical properties of novel poly(diarylamino) styrenes
A series of novel diamines linked by varying conjugated bridges were characterized using FTIR, NMR and UV-visible spectroscopy, mass spectrometry and elemental analysis. The photoluminescence and thermal properties of the compounds were related to structure and quantum chemical calculations were employed to study the optimized ground state geometry of the compounds. The diarylamines exhibited blue to green fluorescence emission and displayed high thermal stability and high glass transition temperature. As such, the compounds might be very useful as hole-transporting materials in organic light-emitting diodes.
Wang, Hai-Ying,Chen, Gang,Xu, Xiao-Ping,Chen, Hua,Ji, Shun-Jun
p. 358 - 365
(2011/06/11)

Molecular rotors as fluorescent viscosity sensors: Molecular design, polarity sensitivity, dipole moments changes, screening solvents, and deactivation channel of the excited states
A library of new fluorescent molecular rotors (FMRs) for viscosity sensing was synthesized. The sensitivity of the fluorescence emission toward solvent viscosity and polarity was investigated by using UV/Vis absorption, fluorescence emission spectra, and theoretical calculations. For the new FMRs, red-shifted emissions at 620 nm, Stokes shifts of 170 nm, and up to 40-fold fluorescence enhancement upon increasing the viscosity of solvents were observed (cf. known FMRs with emissions at 491 nm, Stokes shift of 33 nm and fivefold emission enhancement). By using solvents with high viscosity but low polarity, for example, polyethylene glycol (PEG-400) or dimethyl silicone oil, rotors previously identified as non-FMRs with ethylene glycol/glycerol show FMR properties. We found triphenylamine (TPA)-based rotors showed solvent-polarity-dependent emission, but also FMR properties. This is contrary to the known theory of FMRs. One of the TPA-based rotors shows the highest x value of 0.88 (versus 0.6 for known FMRs). The emissive excited states of the FMRs proved to be locally excited (LE) states and twisted intramolecular charge-transfer (TICT) states were identified as dark states through trifluoroacetic acid titration and DFT/time-dependent DFT calculations, which show that the nonradiative decay channel of the excited FMRs is the rotation about the dicyanovinyl C=C double bonds in the S1 state, not rotation around C-C single bonds. Extension of the π conjugation of the rotors increases the rotation barrier around the C=C double bond in the S1 state (to ca. 50 kJ mol-1 or higher), thus the nonradiative channel is blocked and higher fluorescence quantum yields are observed for the new rotors. Our results will be useful for future design of FMRs as fluorescent viscosity sensors.
Zhou, Fuke,Shao, Jingyin,Yang, Yubin,Zhao, Jianzhang,Guo, Huimin,Li, Xiaolian,Ji, Shaomin,Zhang, Zongying
p. 4773 - 4787
(2011/10/12)

Starburst triarylamine donor-acceptor-donor quadrupolar derivatives based on cyano-substituted diphenylaminestyrylbenzene: Tunable aggregation-induced emission colors and large two-photon absorption cross sections
In this work, we have developed a new class of aggregation-induced emission (AIE) active compounds, in which three electron-donating diphenylamine, phenothiazine, or carbazole groups are connected to the 1, 4-positions of the benzene through bis(α-cyano-4-diphenylaminostyryl) conjugation bridges to form three triarylamine quadrupolar derivatives (3a-c). Their one-and two-photon absorption properties have been investigated. The two-photon absorption (2PA) cross sections measured by the open-aperture Z-scan technique were determined to be 1016, 1484, and 814 GM for 3a-c, respectively. From this result, the high 2PA properties of these molecules are attributed to the extended π system and enhanced intramolecular charge transfer from the starburst triarylamine to the cyano group. Moreover, cyano-substituted diphenylamine styrylbenzene (CNDPASB)-based compounds are very weakly fluorescent in THF, but their intensities increase by almost 230, 70, and 5 times, respectively, in water/THF (v/v 90%) mixtures, in which they exhibit strongly enhanced red, orange, and deep yellow fluorescence emissions, respectively. This result indicates that the intramolecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water, leading to significant increases in fluorescence. It was found that the color tuning of the CNDPASB-based compounds could be conveniently accomplished by changing the starburst triarylamine donor moiety. Multilayer electroluminescence devices with TPBI (2,2′, 2′′-(benzene-1,3,5-triyl)-tri(1-phenyl-1H-benzimidazole)) electron-transporting layers have been made, with 3a and 3c as a non-doping red-yellow emitter. The preliminary results for these multilayer devices show a maximum efficiency of 0.25°, and electroluminescence (EL) wavelengths around 568 nm. The excellent 2PA and AIE properties of these compounds make them potential materials for biophotonic applications.
Wang, Bing,Wang, Yaochuan,Hua, Jianli,Jiang, Yihua,Huang, Jinhai,Qian, Shixiong,Tian, He
experimental part
p. 2647 - 2655
(2011/04/16)

Novel D-π-A system based on zinc-porphyrin derivatives for highly efficient dye-sensitised solar cells
We have designed and synthesised novel zinc porphyrin dyes that have a D-π-A system based on porphyrin derivatives containing a carbazole linked triphenylamine (TPA) electron-donating group as the second electron donor and a meso-substituted phenyl carboxyl anchoring group attached at the meso position of the porphyrin ring, yielding push-pull porphyrins as the most efficient green dye for DSSC applications. Under photovoltaic performance measurements, a maximum photon-to-electron conversion efficiency of 5.01% was achieved with the DSSC based on the dye HKK-Por1 (JSC = 10.7 mA/cm2, V OC = 0.67 V, FF = 0.70) under AM1.5 irradiation (100 mW/cm 2).
Lee, Myung Jun,Seo, Kang Deuk,Song, Hae Min,Kang, Min Soo,Eom, Yu Kyung,Kang, Hong Seok,Kim, Hwan Kyu
supporting information; experimental part
p. 3879 - 3882
(2011/08/09)

Synthesis, two-photon absorption and optical limiting properties of multi-branched styryl derivatives based on 1,3,5-triazine
Five new multi-branched two-photon absorption triazine chromophores (T1-T5) with different donor strength, conjugation length, and direction of charge transfer have been designed and synthesized. The one-photon fluorescence, fluorescence quantum yields, and two-photon properties have been investigated. The two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique were determined to be 447, 854, 1023, 603, and 766GM for T1, T2, T3, T4, and T5, respectively. This result indicates that their 2PA cross section values (I?) increase with increasing electron-donating strength of the end group, extending the conjugation length of the system, and introducing electron-withdrawing perfluoroalkyl as side groups to the end donor. In addition, the I? value of T5 is also larger than that of T1, which provides evidence that the I? value is relative to the direction of charge transfer (from the ends to the center of the molecule or from the center to the ends). Moreover, significant enhancement of the two-photon absorption cross section was achieved by introducing a thiophene moiety to a conjugated Ci￡?C bond. At the same time, the optical limiting behavior for these chromophores was studied by using a focused 800nm laser beam with pulses of 140fs duration. It was found that these molecules also exhibit good optical limiting properties. These initial results clearly demonstrate that multi-branched triazine chromophores are a highly suitable class of two-photon absorbing materials. Limiting the power! A series of new octupolar triazine molecules (T1-T5) containing multibranched styryl derivative moieties have been designed and synthesized. The two-photon absorption cross section values increase with increasing electron-donating strength of the end group, extending the conjugation length of the system, introducing electron-withdrawing perfluoroalkyl as side groups to the end donor, and making charge transfer from the center of the triphenylamine to the triazine ends possible. Copyright
Jiang, Yihua,Wang, Yaochuan,Wang, Bing,Yang, Jiabao,He, Nannan,Qian, Shixiong,Hua, Jianli
experimental part
p. 157 - 165
(2011/10/08)

The photophysical properties and two-photon absorption of novel triphenylamine-based dendrimers
Novel triphenylamine-based dendrimers were synthesized and characterized by FT-IR, elemental analysis, 1H NMR spectroscopy, and MALDI-TOF mass spectrometry. The linear photophysical properties including absorption, one-photon induced fluorescence and the fluorescence lifetimes in different solvents were investigated. The two-photon induced fluorescence behavior was recorded in toluene solution, employing a Ti:sapphire femtosecond laser pulse. The dendrimers both emit strong blue-green fluorescence under irradiation. Two-photon excited state fluorescence cross-sections were also obtained. The two dendrimers displayed a large two-photon absorption. The polytriphenylamine dendrimer shows larger two-photon excited state fluorescence cross-sections in toluene relative to the tristriphenylamine analog, indicating that there is cooperative enhancement originating from inter-branch coupling and an increase of light-harvesting ability with increasing dendrimer size.
Yan, Zi-Qi,Xu, Bin,Dong, Yu-Jie,Tian, Wen-Jing,Li, Ai-Wu
scheme or table
p. 269 - 274
(2011/12/21)

Hole-transporting host-Polymer series consisting of triphenylamine basic structures for phosphorescent polymer light-Emitting diodes
A series of novel styrene derived monomers with triphenylamine-based units, and their polymers have been synthesized and compared with the well-known structure of polymer of N,N′-bis(3-methylphenyl)-N,N′- diphenylbenzidine with respect to their hole-transporting behavior in phosphorescent polymer light-emitting diodes (PLEDs). A vinyltriphenylamine structure was selected as a basic unit, functionalized at the para positions with the following side groups: diphenylamine, 3-methylphenyl-aniline, 1- and 2-naphthylamine, carbazole, and phenothiazine. The polymers are used in PLEDs as host polymers for blend systems with the following device configuration: glass/indium-tin-oxide/PEDOT:PSS/polymer-blend/CsF/Ca/ Ag. In addition to the hole-transporting host polymer, the polymer blend includes a phosphorescent dopant [r(Me-ppy)3] and an electron-transporting molecule (2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole). We demonstrate that two polymers are excellent hole-transporting matrix materials for these blend systems because of their good overall electroluminescent performances and their comparatively high glass transition temperatures. For the carbazole-substituted polymer (Tg = 246 °C), a luminous efficiency of 35 cd A -1 and a brightness of 6700 cd m-2 at 10 V is accessible. The phenothiazine-functionalized polymer (Tg= 220 °C) shows nearly the same outstanding PLED behavior. Hence, both these polymers outperform the well-known polymer of N,N′-bis(3-methylphenyl)-N,N′- diphenylbenzidine, showing only a luminous efficiency of 7.9 cd A-1 and a brightness of 2500 cd m-2 (10 V).
Thesen, Manuel W.,Hoefer, Bianca,Debeaux, Marc,Janietz, Silvia,Wedel, Armin,Anna, Koehler,Johannes, Hans-Hermann,Krueger, Hartmut
scheme or table
p. 3417 - 3430
(2011/05/02)

Tuning the HOMO energy levels of organic dyes for dye-sensitized solar cells based on Br-/Br3- electrolytes
A series of novel metal-free organic dyes TC301-TC310 with relatively high HOMO levels were synthesized and applied in dye-sensitized solar cells (DSCs) based on electrolytes that contain Br-/Br3- and I-/I3-. The effects of additive Li+ ions and the HOMO levels of the dyes have an important influence on properties of the dyes and performance of DSCs. The addition of Li+ ions in electrolytes can broaden the absorption spectra of the dyes on TiO2 films and shift both the LUMO levels of the dyes and the conduction band of TiO2, thus leading to the increase of Jsc and the decrease of Voc. Upon using Br-/Br3- instead of I-/I3-, a large increase of Voc is attributed to the enlarged energy difference between the redox potentials of electrolyte and the Fermi level of TiO2, as well as the suppressed electron recombination. Incident photon to current efficiency (IPCE) action spectra, electrochemical impedance spectra, and nanosecond laser transient absorption reveal that both the electron collection yields and the dye regeneration yields (Φr) depend on the potential difference (the driving forces) between the oxidized dyes and the Br-/Br 3- redox couple. For the dyes for which the HOMO levels are more positive than the redox potential of Br-/Br3 - sufficient driving forces lead to the longer effective electron-diffusion lengths and almost the same efficient dye regenerations, whereas for the dyes for which the HOMO levels are similar to the redox potential of Br-/Br3-, insufficient driving forces lead to shorter effective electron-diffusion lengths and inefficient dye regenerations. A new middleman: The Br-/Br3- redox mediator was proved to be a promising alternative to I-/I 3- for application in dye-sensitized solar cells (see graphic). Studies show that the energy gap between the HOMO level of the dye and the potential of the Br-/Br3- redox mediator influences their charge-transfer processes and solar-energy conversion efficiency.
Teng, Chao,Yang, Xichuan,Li, Shifeng,Cheng, Ming,Hagfeldt, Anders,Wu, Li-Zhu,Sun, Licheng
supporting information; experimental part
p. 13127 - 13138
(2011/02/24)

Multibranched triarylamine end-capped triazines with aggregation-induced emission and large two-photon absorption cross-sections
Multibranched triarylamine derivatives with a 1,3,5-triazine core have been synthesized and exhibit aggregation-induced emission and a large two-photon absorption cross section (8629 GM).
Jiang, Yihua,Wang, Yaochuan,Hua, Jianli,Tang, Jin,Li, Bo,Qian, Shixiong,Tian, He
supporting information; experimental part
p. 4689 - 4691
(2010/09/05)

Ethynylated triphenylamine monoboronic acid chemosensors: Experimental and theoretical studies
New ethynylated triphenylamine boronic acid sensors 1 and 2 were designed and the photophysical properties, as well as the binding with tartaric acid and mandelic acid were studied. We found the emission intensity of the sensors is sensitive to the polarity of the solvents and the emission of sensor 2 is sensitive to protic solvents. Theoretical calculations on the low-lying excited states of these sensors predicted d-PET effect. Experimental observations show either a-PET effect or no significant PET effect for the sensors. The sensitivity of the emission of the sensors toward solvent polarity is used to rationalize the observed emission intensity-pH profiles.
Chi, Lina,Wu, Yubo,Zhang, Xin,Ji, Shaomin,Shao, Jingyin,Guo, Huimin,Wang, Xin,Zhao, Jianzhang
experimental part
p. 1255 - 1265
(2011/11/04)

Synthesis and photovoltaic properties of novel solution-processable triphenylamine-based dendrimers with sulfonyldibenzene cores
Three conjugated dendrimers containing electron-accepting sulfonyldibenzene (SDB) cores and electron-donating triphenylamine dendrons have been synthesized through a convergent synthetic strategy without any protection/deprotection chemistry. The dendrimers were highly soluble in common organic solvents, and could form good quality optical films by spin coating. Their thermal, optical and electrical properties are manipulated by attaching different peripheral dendrons. Using these dendrimers as donors and [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as acceptor, the bulk heterojunction solar cells with a structure of ITO-PEDOT-dendrimers:PCBM-LiF-Al were fabricated. The cell based on dendrimer G0 shows a relatively high power-conversion efficiency (PCE) of 0.34% under AM 1.5 illumination of 100 mW cm-2.
Li, Kunpeng,Qu, Jiali,Xu, Bin,Zhou, Yinhua,Liu, Leijing,Peng, Ping,Tian, Wenjing
experimental part
p. 2120 - 2127
(2009/12/25)

Synthesis, characterization, two-photon absorption, and optical limiting properties of triphenylamine-based dendrimers
Three π-conjugated dendrimers (Ph-G0, Ph-G1 and Ph-G2) bearing triphenylamine moieties have been synthesized through a convergent synthetic strategy without any protection-deprotection chemistry. The linear photophysical properties, two-photon absorption (TPA), and optical limiting behavior of the dendrimers were investigated in solution at room temperature. Linear absorption and emission spectra revealed a bathochromic shift and decreased fluorescence quantum yields with increasing dendrimer generation. A strong cooperative effect in the TPA absorption of these dendrimers was observed. The TPA cross-sections increase gradually with the proportion of triphenylamine units and the maximum value of the TPA cross-section can reach 5690 GM for Ph-G2. These triphenylamine-based dendrimers exhibited efficient two-photon optical limiting under femtosecond excitation.
Xu, Bin,Fang, Honghua,Chen, Feipeng,Lu, Hongguang,He, Jiating,Li, Yaowen,Chen, Qidai,Sun, Hongbo,Tian, Wenjing
experimental part
p. 2457 - 2464
(2010/03/04)

A facile convergent procedure for the preparation of triphenylamine-based dendrimers with truxene cores
A simple convergent procedure has been developed for the preparation of triphenylamine dendrons containing an alkene at the center, which can be coupled in a single step to give dendrimers that contain truxene for the core without any protection-deprotection chemistry. These conjugated dendrimers exhibit similar absorption and emission behaviors in solutions and in thin films, which are indicative of the high isolation effect of well-organized three-dimensional dendrimers. They also have high fluorescence quantum yields and high glass transition temperatures, which indicate that these dendrimers are candidates for the application in OLED as light emitting materials.
Xia, Haijian,He, Jiating,Xu, Bin,Wen, Shanpeng,Li, Yaowen,Tian, Wenjing
p. 5736 - 5742
(2008/09/21)

Synthesis and photophysical properties of triphenylamine-based dendrimers with 1,3,5-triphenylbenzene cores
Two new conjugated dendrimers bearing a triphenylamine moiety as dendrons and 1,3,5-triphenylbenzene as a core have been synthesized through a convergent synthetic strategy. These conjugated dendrimers have high fluorescence quantum yields and exhibit similar absorption and emission behaviors in solutions and in solid films, which demonstrate that these dendrimers form good amorphous states.
Xia, Haijian,He, Jiating,Peng, Ping,Zhou, Yinhua,Li, Yaowen,Tian, Wenjing
p. 5877 - 5881
(2008/02/09)

The synthesis of robust, polymeric hole-transport materials from oligoarylamine substituted styrenes
Novel styrene-based oligoarylamine monomers are described which are suitable for the preparation of polymeric hole-transport materials, with very high glass transition temperatures. The monomers are prepared using the Wittig reaction from the appropriate aldehyde precursor, which was assembled using the classical Ullmann reaction. A number of the monomers yielded high-quality crystals which facilitated X-ray characterisation. Polymerisation was achieved either by solution free-radical initiation or by condensed phase thermal autopolymerisation. The latter suggests a method of initiator-free polymerisation which may have potential for multilayer device fabrication. The Royal Society of Chemistry.
McKeown, Neil B.,Badriya, Samer,Helliwell, Madeleine,Shkunov, Maxim
p. 2088 - 2094
(2008/02/07)

Synthesis and properties of new chiral donor-embedded polybinaphthalenes for nonlinear optical applications
Eight new chiral, chromophore-functionalized donor-embedded polybinaphthalenes were prepared and characterized for their (nonlinear) optical properties. The polymers were prepared by direct polymerization using a Stille coupling reaction between a chiral bis(trimethyltin) binaphthalene derivative and diiodo-functionalized chromophores. The use of diiodo-functionalized instead of dibromo-functionalized chromophores resulted in a significant increase of molecular weight, as demonstrated by end group analysis, GPC, and MALDI-TOF experiments. The reaction conditions allowed the use of a great variety of chromophores with different DπA structures. The typical treelike macromolecular architecture of the polymers is reflected in the behavior of the glass transition temperature and, more clearly, in the nonlinear optical properties. The nonlinear optical response shows a continuous, linear increase in function of chromophore concentration, indicating that the dipolar interactions between the chromophores are eliminated. Moreover, chiral contributions to the nonlinear optical response were observed and mounted 14% of the highest achiral contribution.
Koeckelberghs, Guy,Vangheluwe, Marnix,Picard, Isabel,De Groof, Leen,Verbiest, Thierry,Persoons, Andre,Samyn, Celest
p. 8530 - 8537
(2007/10/03)