201802-29-1Relevant articles and documents
Aggregation induced emission of diketopyrrolopyrrole (DPP) derivatives for highly fluorescent red films
Hwang, Tae Gyu,Kim, Jeong Yun,Namgoong, Jin Woong,Lee, Jae Moon,Yuk, Sim Bum,Kim, Se Hun,Kim, Jae Pil
, p. 1064 - 1074 (2019)
A large number of diketopyrrolopyrrole (DPP) compounds showing aggregation induced emission (AIE) have been reported in the past few years. However, although DPP compounds exhibited AIE and excellent luminescence properties, their luminescence properties in solid or film states were not much focused on. Here we synthesized and characterized a series of DPP compounds with triphenylamine (TPA) moieties to investigate the AIE properties in the solid film state depending on the functional groups (TPA, BTPA, and MTPA) attached to the TPA moieties. T2 and D2 thin films showed excellent fluorescence quantum yields of 31% and 26%, respectively, compared to an M2 thin film (9%). The restriction of an intramolecular rotation process could inhibit the aggregation induced quenching process and play a key role in achieving highly fluorescent molecules in the solid state.
The Diradical-Dication Strategy for BODIPY- and Porphyrin-Based Dyes with Near-Infrared Absorption Maxima from 1070 to 2040 nm
Wei, Houjia,Feng, Rui,Fang, Yong,Wang, Lei,Chen, Chao,Zhang, Li,Cui, Haiyan,Wang, Xinping
, p. 19341 - 19347 (2018)
Four stable boron dipyrromethene (BODIPY)- and porphyrin-based bis-arylamine diradical dications were synthesized by two-electron oxidation of their neutral molecules. The two BODIPY-based dications have open-shell singlet ground states. UV/Vis absorption spectra of all four dications showed large redshifts in the NIR region compared to their neutral precursors with absorption maxima at 1274 and 1068 nm for the two BODIPY-based dications and 1746 and 2037 nm for the two porphyrin-based dications. Thus, two new types of NIR dyes with longer wavelengths are provided by the diradical-dication strategy, which can be applied for the generation of other NIR dyes with a range of different chromophores and auxochromes.
Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption
Fakis, Mihalis,Georgiou, Dimitris,Gyepes, Róbert,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Smolí?ek, Maro?
supporting information, p. 5512 - 5517 (2021/07/31)
Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.
Hole transport material based on tetraarylbutadiene, preparation method and applications thereof
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Paragraph 0119; 0129-0131, (2020/02/29)
The invention discloses a hole transport material based on tetraarylbutadiene, wherein the hole transport material has a chemical general formula represented by a formula (I), and is an organic smallmolecule using tetraphenyl butadiene, tetrathiophene butadiene or tetrafuran butadiene as a core and using alkoxy or alkylthio substituted diphenylamine, triphenylamine, carbazole, phenothiazine or phenoxazine as a side group. According to the invention, the preparation method of the hole transport material has characteristics of simple synthesis and low cost, and has the potential of large-scaleproduction; and the hole transport material has good photoelectric property and good thermal stability, can be used as a hole transport material to be applied to photoelectric devices such as organicphotoconductive drums, OLED display devices, solar cells and the like, and has great application prospects.
Highly solvatochromic fluorescence of anthraquinone dyes based on triphenylamines
Li, Yanxia,Tan, Tingfeng,Wang, Shirong,Xiao, Yin,Li, Xianggao
, p. 262 - 270 (2017/06/05)
Five donor-acceptor anthraquinone dyes based on phenylamine/triphenylamines with different substituted groups were synthesized by Suzuki reaction in good yields, and the photophysical properties were studied in organic solvents with different polarity. The title dyes exhibited remarkable solvatochromic fluorescence (>190 nm emission shift in polar media), which was derived from intramolecular charge transfer (ICT) character that revealed by DFT/TD-DFT calculation. And large Stokes shifts (210–306 nm) were observed in different organic solvents, along with rich color changes from blue to green, yellow, orange and even purple-red. The Stokes shifts were linearly dependent on the solvent polarity function ET(30). Interestingly, it was found from the single-crystal X-ray diffraction analysis that dye 3 displayed two different interleaved channel structures, which was seldom seen in organic compounds and could be used as host for complexation potentially. Electrochemical characterization suggested that the different substituted phenylamine groups attached to anthraquinone unit could lead to tunable potentials and energy levels.
Organic chromophores based on a fused bis-thiazole core and their application in dye-sensitized solar cells
Dessi, Alessio,Barozzino Consiglio, Gabriella,Calamante, Massimo,Reginato, Gianna,Mordini, Alessandro,Peruzzini, Maurizio,Taddei, Maurizio,Sinicropi, Adalgisa,Parisi, Maria Laura,Fabrizi De Biani, Fabrizia,Basosi, Riccardo,Mori, Riccardo,Spatola, Michele,Bruzzi, Mara,Zani, Lorenzo
supporting information, p. 1916 - 1928 (2013/05/08)
Four new D-π-A organic dyes incorporating either a thiazolo[5,4-d] thiazole bicyclic system (TTZ1-2) or a benzo[1,2-d:4,5-d′]bisthiazole tricyclic unit (BBZ1-2) have been synthesized and fully characterized. The key steps of the synthesis include an efficient MW-assisted preparation of the thiazolo[5,4-d]thiazole core and selective functionalization of two different dihalothienyl derivatives through Suzuki coupling. All the compounds showed photo- and electrochemical properties compatible with their employment in dye-sensitized solar cells. In addition, their electronic structure and transitions were investigated by means of TD-DFT calculations. Dye-sensitized solar cells fabricated with dye TTZ1 yielded an average power conversion efficiency corresponding to 43 and 60 % of the performances recorded under the same conditions for cells containing reference dyes N3 and D5, respectively. Efficiency measurements and electrochemical impedance spectroscopy (EIS) experiments indicated that use of chenodeoxycholic acid (CDCA) as a co-adsorbent was beneficial to disrupt dye-dye interactions and slow down recombination processes within the cells, thus allowing power conversion efficiencies up to 3.53 % to be obtained. Four D-π-A dyes incorporating fused-heterocyclic ring systems, such as thiazolothiazoles and benzobisthiazoles, have been synthesized and characterized. Their incorporation into dye-sensitized solar cells yielded devices with power conversion efficiencies up to 3.53 %. The average efficiencies of the cells were 43 and 60 % those of cells containing the reference dyes N3 and D5, respectively.
Synthesis and photoelectric properties of a novel perylene diimide derivative
Yi, Si-Li,Xu, Qing
, p. 7355 - 7360 (2013/08/23)
A novel donor-acceptor-donor (D-A-D) perylene diimide derivative 1,7-bis-[N,N-bis-(4-methoxy phenyl)aniline]perylene diimide (PDI2) had been successfully synthesized by means of bromination, condensation, Suzuki-crossing reaction. 1,7-Bis-[N,N-bis-(4-methoxy phenyl)aniline]perylene diimide exhibits excellent solubility in common solvents. The absorption maxima of PDI2 shows a bathochromic shift and absorption bands span widen to 890 nm, due to the introduction of electron donating bis-(4-methoxyphenyl)phenylamine moiety. A pronounced fluorescence quenching was observed due to the intramolecular charge transfer. Cyclic voltammograms of PDI2 display a couple of reversible redox peaks. The LUMO and HOMO levels of PDI2 were calculated as -3.88 eV and -5.13 eV, respectively.
Efficient and stable dye-sensitized solar cells based on phenothiazine sensitizers with thiophene units
Wu, Wenjun,Yang, Jiabao,Hua, Jianli,Tang, Jin,Zhang, Lei,Long, Yitao,Tian, He
supporting information; experimental part, p. 1772 - 1779 (2010/08/19)
Three new phenothiazine organic dyes containing thiophene, 3-(5-(3-(4-(bis(4-methoxy phenyl)amino)phenyl)-10-octyl-10H-phenothiazin-7-yl) thiophen-2-yl)-2-cyanoacrylic acid (P1), 3-(5-(3-(4-(diphenylamino)phenyl)-10- octyl-10H-phenothiazin-7-yl)thiophen-2-yl)-2-cyanoacrylic acid (P2) and 2-cyano-3-(5-(10-octyl-3-(4-(2,2-diphenylvinyl)phenyl)-10H-phenothiazin-7-yl) thiophen-2-yl) acrylic acid (P3) were designed and synthesized as sensitizers for application in dye-sensitized solar cells (DSSCs). For these dyes, the phenothiazine derivative moiety and the cyanoacetic acid take the roles of electron donor and electron acceptor, respectively. The absorption spectra, electrochemical and photovoltaic properties of P1-P3 and the cell long-term stability were extensively investigated. It was found that HOMO and LUMO energy level tuning can be conveniently accomplished by alternating the donor moiety. The DSSCs based on dye P2 showed the best photovoltaic performance: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 84.9%, a short-circuit photocurrent density (Jsc) of 10.84 mA cm -2, an open-circuit photovoltage (Voc) of 592 mV, and a fill factor (ff) of 0.69, corresponding to an overall conversion efficiency of 4.41% under standard global AM 1.5 solar light conditions. These results demonstrated that the DSSCs based on phenothiazine dyes could achieve both high performance and good stability.
Structure-property relationships in conjugated donor-acceptor molecules based on cyanoanthracene: Computational and experimental studies
Lin, Jui-Hsien,Elangovan, Arumugasamy,Ho, Tong-Ing
, p. 7397 - 7407 (2007/10/03)
Two series of π-conjugated bipolar compounds, namely, 9-phenyl-10-anthronitriles (PAN series) and 9-phenylethynyl-10-anthronitriles (PEAN series), having inherent redox centers have been synthesized and their electronic absorption, fluorescence emission,
