- Photoresponsive porous materials: The design and synthesis of photochromic diarylethene-based linkers and a metal-organic framework
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The synthesis and characterization of novel photochromic diarylethene-based linkers for use in metal-organic frameworks is described including crystal structure analysis of nearly all reaction intermediates. The bis-carboxylated dithien-3-ylphenanthrenes can be prepared under relatively mild conditions in high yield and were subsequently used to create a photoresponsive metal-organic framework, UBMOF-1. While the photochromism of the ligand TPDC in solution is fully reversible, the cycloreversion reaction is suppressed when this linker is incorporated into the crystalline framework of UBMOF-1. The Royal Society of Chemistry 2014.
- Patel, Dinesh G.,Walton, Ian M.,Cox, Jordan M.,Gleason, Cody J.,Butzer, David R.,Benedict, Jason B.
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Read Online
- Redox Mechanisms in Li and Mg Batteries Containing Poly(phenanthrene quinone)/Graphene Cathodes using Operando ATR-IR Spectroscopy
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The redox reaction mechanism of a poly(phenanthrene quinone)/graphene composite (PFQ/rGO) was investigated using operando attenuated total reflection infrared (ATR-IR) spectroscopy during cycling of Li and Mg batteries. The reference phenanthrene quinone and the Li and Mg salts of the hydroquinone monomers were synthesized and their IR spectra were measured. Additionally, IR spectra were calculated using DFT. A comparison of all three spectra allowed us to accurately assign the C=O and C?O? vibration bands and confirm the redox mechanism of the quinone/Li salt of hydroquinone, with radical anion formation as the intermediate product. PFQ/rGO also showed exceptional performance in an Mg battery: A potential of 1.8 V versus Mg/Mg2+, maximum capacity of 186 mAh g?1 (335 Wh kg?1 of cathode material), and high capacity retention with only 8 % drop/100 cycles. Operando ATR-IR spectroscopy was performed in a Mg/organic system, revealing an analogous redox mechanism to a Li/organic cell.
- Vizintin, Alen,Bitenc, Jan,Kopa? Lautar, Anja,Grdadolnik, Jo?e,Randon Vitanova, Anna,Pirnat, Klemen
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- Effect of side chains on phenanthrene based D-A type copolymers for polymer solar cells
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A series of low band gap conjugated copolymers containing 9,10-modified phenanthrene and diketopyrrolopyrrole (DPP) units were synthesized as electron donor materials for bulk heterojunction organic solar cells. These donor-acceptor type PDPP copolymers have varying solubilizing groups on their identical conjugated backbones. The optical bandgap of PDPP copolymers is about 1.6?eV which corresponds to the long wavelength region of the solar spectrum. Through the incorporation of phenanthrene units into the conjugated backbone instead of commonly used thiophene derivatives, a higher open-circuit voltage of about 0.8?V could be achieved, as a result of their deeper HOMO level. Of all the devices, the P4:PC61BM BHJ system showed the best performance with a Voc of 0.79?V, a Jsc of 5.97?mA?cm?2, a fill factor of 0.62 and a power conversion efficiency of 2.73% due to superior nanoscale phase separation between the electron donor and electron acceptor materials than in the other polymers arising from short-branched solubilizing groups on the phenanthrene side of its conjugated backbone.
- Kim, Yeong-A.,Hwang, Kyeong-Il,Kang, Minji,Kim, Nam-Koo,Jang, Soo-young,Kim, In-Bok,Kim, Juhwan,Kim, Dong-Yu
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- The effect of the donor unit on the optical properties of polymers
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A series of donor-acceptor-donor (DAD) type π-conjugated monomers containing 10,11,12,13-tetrahydrodibenzo[a,c]phenazine moiety in the backbone as the acceptor unit and thiophene derivatives as the donor unit were prepared by Stille coupling. Thiophene, 3-hexyl thiophene and 3,4-ethylenedioxythiophene were used as the donor units to understand the effects of donor unit on electrochemical and optoelectronic properties of the resulting polymers. Electroactivity of monomers and redox behavior of their polymers were investigated by cyclic voltammetry. The presence of the strong electron-donating ethylenedioxy groups on the aromatic structure increased electron density on 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-10,11,12,13- tetrahydrodibenzo[a,c]phenazine (DTBP), thus the oxidation potential of DTBP shifts to a lower value than that of 2,7-bis(4-hexylthiophen-2-yl)-10,11,12,13- tetrahydrodibenzo[a,c] phenazine (HTBP) and 2,7-di(thiophen-2-yl)-10,11,12,13- tetrahydrodibenzo[a,c]phenazine (TTBP). The electronic band gaps, defined as the onset of the π-π transition, were found to be 2.5 eV for HTBP, 2.0 eV for DTBP and 2.2 eV for TTBP. Both of PDTBP and PTTBP films showed multi-color electrochromism and also fast switching times (1 s) in the visible and NIR regions.
- Unver, Elif Kose,Tarkuc, Simge,Udum, Yasemin Arslan,Tanyeli, Cihangir,Toppare, Levent
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Read Online
- Synthesis of Redox-Active Photochromic Phenanthrene Derivatives
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A phenanthrene unit has been functionalized by several methylthiophene units in order to bring it a photochromic behavior. These compounds were characterized by NMR, absorption and emission spectroscopies, theoretical calculations as well as cyclic voltammetry. The association of a phenanthrene group with a photochromic center could open the door to a new generation of organic field-effect transistors.
- Chatir, Elarbi,Boggio-Pasqua, Martial,Loiseau, Frederique,Philouze, Christian,Royal, Guy,Cobo, Saioa
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supporting information
(2021/12/24)
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- Unexpected radical mechanism in a [4+1] cycloaddition reaction
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9,10-Phenanthrenequinone monoimines (2,7-R-PQI, R = tBu, H, Br, NO2, 1a-d) undergo a [4+1] cycloaddition reaction with triphenylphosphine to give 2,3-dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2λ5-oxazaphospholes (3a-d). During the reaction, highly colored radicals are formed as intermediates, which were characterized by EPR and UV-vis spectroscopy. The formation rate and the rate of decay of these radicals were determined kinetically. These radicals exhibit high persistency and under inert conditions can be handled conveniently. Based on detailed kinetic and spectroscopic studies and DFT calculations, a plausible mechanism has been proposed. This journal is
- Bors, István,Purgel, Mihály,Fehér, Péter Pál,Varga, Tamás,Speier, Gábor,Korecz, László,Kaizer, József
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p. 8440 - 8444
(2021/05/25)
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- Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines
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This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).
- Bao, Ming,He, Min,Wang, Yi,Yu, Xiaoqiang
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p. 14720 - 14731
(2021/11/16)
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- Metal-Free Catalysis: A Redox-Active Donor-Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2Reduction to CH4
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Achieving more than a two-electron photochemical CO2reduction process using a metal-free system is quite exciting and challenging, as it needs proper channeling of electrons. In the present study, we report the rational design and synthesis of
- Barman, Soumitra,Singh, Ashish,Rahimi, Faruk Ahamed,Maji, Tapas Kumar
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supporting information
p. 16284 - 16292
(2021/10/12)
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- UV to NIR multistate electrochromism and electrofluorochromism in dibenzophenazine-arylamine derivatives
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An intriguing case of intramolecular and intervalence charge transfer-driven multistate electrochromism and electrofluorochromism in dibenzophenazin-(phenyl)methanone and arylamine-based redox-active donor-acceptor-donor molecules was elucidated. Tunable
- Patra, Abhijit,Sarkar, Madhurima,Sengupta, Arunava,Singh, Kuldeep,Sk, Bahadur
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supporting information
p. 13590 - 13593
(2021/12/23)
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- Green light compound based on dibenzophenazine, preparation method and device thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a green light compound based on dibenzophenazine, a preparation method and a device thereof. The invention provides the green light compound based o
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Paragraph 0033-0035
(2021/08/07)
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- Precise membrane separation of nanoparticles using a microporous polymer containing radially π-conjugated molecular carbocycles
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Herein, we report the synthesis of a novel porous polymer, PS2, containing radially π-conjugated carbocycles and a linear phenylene backbone. The PS2-based membrane has a distinct small size cutoff (ca. 2.6 nm) and a major size at ～1.5 nm for the size-sel
- Du, Pingwu,Fang, Pengwei,Huang, Pingsen,Huang, Qiang,Wang, Jinyi,Wang, Shengda
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p. 11867 - 11870
(2021/11/30)
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- N-Rich electron acceptors: triplet harvesting in multichromophoric pyridoquinoxaline and pyridopyrazine-based organic emitters
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Controlling the nonradiative deactivation of triplet states and tuning the singlet-triplet energy gap are the major challenges in developing materials that exhibit thermally activated delayed fluorescence (TADF) and room temperature phosphorescence (RTP). Additionally, the conformational flexibility/rigidity around the donor-acceptor bond and the π-spacer unit significantly alters the charge transfer efficiency, subsequently impacting the relative propensity of TADF and RTP. Herein, we propose a new class of multichromophoric tridonor-acceptor (D3-A) compounds with rigid and flexible π-spacers having N-rich pyridoquinoxaline and pyridopyrazine acceptor cores, respectively. The molecule with carbazole donorsmetato the quinoxaline nitrogen of the rigid pyridoquinoxaline core exhibits TADF, whereas the variation of the linkage position of carbazole to the pyridoquinoxaline as well as the twisted and flexible pyridopyrazine core shows predominantly RTP due to a relatively higher singlet-triplet energy gap. Increasing the donor strength with phenoxazine in the pyridopyrazine system leads to TADF and RTP simultaneously. Furthermore, we demonstrate the promising scope of the all-organic triplet harvesting materials in solid-state security encryption.
- James, Anto,Kundu, Subhankar,Patra, Abhijit,Sharma, Samarth,Sk, Bahadur
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supporting information
p. 12943 - 12950
(2020/10/18)
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- Crown ether-containing carboxylic acid compound BPDC-12-C-4, preparation method and application thereof
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The invention relates to a crown ether-containing carboxylic acid compound BPDC-12-C-4, and belongs to the field of organic chemical synthesis. The preparation method comprises the following steps of:stirring and adding N-bromosuccinimide (NBS) into 9, 10-phenanthrenedione to synthesize a compound 1, dissolving the compound 1 into tetrahydrofuran, after the reaction is finished, conducting ethylacetate extraction and rotary evaporation to obtain a compound 2, dissolving the compound 2 into N, N-dimethylformamide (DMF), then adding 1, 2-bis(2-chloroethoxy)ethane and potassium carbonate to obtain a compound 3, dissolving the compound 3 by using N, N-dimethylacetamide (DMA), injecting the product into a reaction bottle filled with cuprous cyanide to obtain a compound 4, dissolving the compound 4 and sodium hydroxide into a mixed solvent, conducting stirring reflux, and finally removing the solvent, adjusting the PH value, conducting suction filtration, washing and drying to obtain BPDC-12-C-4. The BPDC-12-C-4 can be used as a ligand for synthesizing a metal organic framework material, that is, a crown ether derivative is embedded into the ligand of the metal organic framework material, and the BPDC-12-C-4 shows huge application prospects in the aspects of catalysis, gas adsorption and separation and the like.
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Paragraph 0021-0022
(2020/10/20)
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- Solid state multicolor emission in substitutional solid solutions of metal-organic frameworks
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Preparing crystalline materials that produce tunable organic-based multicolor emission is a challenge due to the inherent inability to control the packing of organic molecules in the solid state. Utilizing multivariate, high-symmetry metal-organic frameworks, MOFs, as matrices for organic-based substitutional solid solutions allows for the incorporation of multiple fluorophores with different emission profiles into a single material. By combining nonfluorescent links with dilute mixtures of red, green, and blue fluorescent links, we prepared zirconia-Type MOFs and found that the bulk materials exhibit features of solution-like fluorescence. Our study found that MOFs with a fluorophore link concentration of around 1 mol % exhibit fluorescence with decreased inner filtering, demonstrated by changes in spectral profiles, increased quantum yields, and lifetime dynamics expected for excited-state proton-Transfer emitters. Our findings enabled us to prepare organic-based substitutional solid solutions with tunable chromaticity regulated only by the initial amounts of fluorophores. These materials emit multicolor and white light with high quantum yields (-2-14%), high color-rendering indices (>93), long shelf life, and superb hydrolytic stability at ambient conditions.
- Newsome, Wesley J.,Ayad, Suliman,Cordova, Jesus,Reinheimer, Eric W.,Campiglia, Andres D.,Harper, James K.,Hanson, Kenneth,Uribe-Romo, Fernando J.
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supporting information
p. 11298 - 11303
(2019/08/07)
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- MULTIVARIATE METAL-ORGANIC FRAMEWORKS FOR FINE-TUNING LIGHT EMISSION
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Multivariate metal-organic framework compositions and methods of producing multivariate metal-organic frameworks. The metal-organic framework including at least one light-emitting linker in an amount sufficient for the composition to produce broadband emission spectra in high efficiencies.
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Page/Page column 37-39
(2019/07/13)
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- T and V-shaped donor-acceptor-donor molecules involving pyridoquinoxaline: Large Stokes shift, environment-sensitive tunable emission and temperature-induced fluorochromism
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The intramolecular charge transfer-driven emission properties of T and V-shaped donor-acceptor-donor molecules involving a new acceptor core of pyridoquinoxaline were demonstrated. The T-shaped molecule exhibits a large Stokes shift, red emission in the solid state and remarkable viscosity and temperature-dependent tunable fluorescence including a thermally-induced single-component near white-light emission.
- Sk, Bahadur,Khodia, Saurabh,Patra, Abhijit
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supporting information
p. 1786 - 1789
(2018/02/21)
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- Dibenzo-benzimidazole derivative and application thereof
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The invention provides dibenzo-benzimidazole derivatives and application thereof, and relates to the technical field of organic optoelectronic materials. The compounds are a series of dibenzo-benzimidazole derivatives which adopt imidazole as a mother nucleus structure modified with a substituent group. The dibenzo-benzimidazole derivatives are simple in preparation method and easy in raw material obtaining, can be used as main body materials applied to OLED (Organic Light Emitting Diode) devices, can improve the light emission efficiency of the devices and reduce driving voltage to a certain extent, and are organic electroluminescence materials with excellent properties.
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Paragraph 0113-0114
(2017/12/27)
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- Structure-property relationship of D-A type copolymers based on phenanthrene and naphthalene units for organic electronics
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Four donor-acceptor (D-A) type conjugated polymers (PA1, PA2, PA3 and PA4) based on phenanthrene and naphthalene as the donating units with or without dimethoxy substitution were synthesized for organic field effect transistors (OFETs) and bulk-heterojunction organic photovoltaics (OPVs). Dimethoxy substituents have significant effects on the optical, electrochemical, charge transport and photovoltaic properties depending on the donor-polyaromatic (PA) compounds. The optical band gaps of these PA-based copolymers from the smallest to the largest are as follows: 1.52 eV (1,5-dimethoxy substituted naphthalene (PA4)), 1.59 eV (unsubstituted naphthalene (PA3)), and 1.63 eV (unsubstituted phenanthrene (PA1), and substituted 9,10-dimethoxy phenanthrene (PA2)). While the values vary depending on the compounds, both PA2 and PA4 are found to have higher highest occupied molecular orbital (HOMO) energy levels than those of PA1 and PA3 due to the electron donating nature of dimethoxy substituents. The PA based copolymers without dimethoxy substituents showed highly balanced ambipolar behavior with ～1 cm2 V-1 s-1, whereas the electron mobility of dimethoxy modified PA (MeOPA) based copolymers was suppressed. The inverted bulk heterojunction OPVs based on PA1 and PA3 exhibited power conversion efficiency (PCE) as high as 5.3% and 5.8%, respectively. The PCEs of PA copolymer-based OPV devices were mainly affected by an increase in the open circuit voltage rather than by the photocurrent or fill factor.
- Kim, Yeong-A,Kang, Minji,Jeon, Ye-Jin,Hwang, Kyeongil,Kim, Yeon-Ju,Jang, Soo-Young,Kim, In-Bok,Kwon, Gucheol,Kim, Dong-Yu
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supporting information
p. 10332 - 10342
(2017/10/19)
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- COMPOUND HAVING DIAZATRIPHENYLENE RING STRUCTURE, AND ORGANIC ELECTROLUMINESCENT DEVICE
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A compound that emits fluorescence and delayed fluorescence is provided as a material for an organic electroluminescent device of high efficiency, and an organic photoluminescent device and an organic electroluminescent device of high efficiency and high luminance are provided using this compound. The compound of a general formula (1) having a diazatriphenylene ring structure is used as a constituent material of at least one organic layer in the organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.
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- 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer of the polymer and its preparation method
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The invention relates to a 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, a preparation method of the 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer, and a polymer. The 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer has a large pi conjugation rigid plane and stronger electron affinity. The introduction of 2,7-alkyl has a critical effect in improving performances, such as molecular weight, solubility, processibility or self-assembly, of the monomer or the relevant polymer. The 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer is synthesized by phenanthraquinone bromination, reduction, hydroxyl protection, 2,7-alkylation, fuming nitric acid oxidation deprotection, ring closing and the like, and is easy to synthesize and purify, raw materials are low in price, and the mass production is facilitated. A homopolymer or a copolymer can be obtained by Suzuki, Stille or Yamamoto polymerization reaction of the 2,7-alkyl substituted phenanthro [9,10-b] pyrazine derivative monomer. The series of polymers have good solubility in an organic solvent, are suitable for solution processing, and have wide application prospects in the fields of organic panel display, photovoltaic batteries, and organic field effect transistors.
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Paragraph 0034-0036
(2017/03/08)
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- An organic electron transport compound
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The invention provides an organic electronic transmission compound having a following structural formula (I) as shown in the specification. The organic electronic transmission compound is better in thermal stability, is high in luminous efficiency and purity, can be used for manufacturing an organic electroluminescence device and is applied to the field of organic solar batteries, organic thin film transistors or organic photoreceptors..
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Paragraph 0065; 0066; 0067
(2016/10/07)
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- A benzimidazole-based electron transport compound
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The invention provides a benzimidazole-based electron transport compound with a structure formula I. The compound has the advantages of relatively good thermal stability, high luminous efficiency and high luminous purity. The compound can be used for manufacturing an organic electroluminescent device and can be applied in the fields of organic solar cells, organic thin-film transistors or organic photoreceptors. The structure formula I is as shown in the specification.
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Paragraph 0061; 0063; 0069-0071
(2016/10/10)
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- Bottom-up solution synthesis of narrow nitrogen-doped graphene nanoribbons
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Large quantities of narrow graphene nanoribbons with edge-incorporated nitrogen atoms can be synthesized via Yamamoto coupling of molecular precursors containing nitrogen atoms followed by cyclodehydrogenation using Scholl reaction. the Partner Organisati
- Vo, Timothy H.,Shekhirev, Mikhail,Kunkel, Donna A.,Orange, Fran?ois,Guinel, Maxime J.-F.,Enders, Axel,Sinitskii, Alexander
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supporting information
p. 4172 - 4174
(2014/04/17)
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- A soluble ladder-conjugated star-shaped oligomer composed of four perylene diimide branches and a fluorene core: Synthesis and properties
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A new ladder-conjugated star-shaped oligomer electron-transporting material TetraPDI-PF, with four perylene diimide (PDI) branches and a fluorene core, was efficiently synthesized. The oligomer is highly soluble in dichlorobenzene with a solubility of 155 mg mL-1, which is higher than those of PDI (35 mg mL-1) and PDI-Phen (70 mg mL-1). Demonstrated by thermogravimetric analysis (TGA), the oligomer exhibits excellent thermal stability with the decomposition temperature (Td) of 291.2 °C, which is 65 °C higher than that of PDI. Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) were employed to investigate the electrochemical properties. Although the CV curves of TetraPDI-PF are successively scanned for 15 cycles, they still remain invariable reduction potentials. The oligomer also shows outstanding photostability, even better than PDI, which maintains 99 % fluorescence intensity after irradiation for 10 min using maximum laser intensity. In the steady-state space-charge-limited current (SCLC) devices, TetraPDI-PF exhibits higher intrinsic electron mobility of 2.22×10-5 cm2 V-1 s-1, three orders of magnitude over that of PDI (3.52×10-8 cm2 V-1 s-1). The bulk heterojunction (BHJ) organic solar cells (OSCs) using TetraPDI-PF as non-fullerene acceptors and P3HT as donors give optimum power conversion efficiency (PCE) of 0.64 %, which is 64 times that of the PDI:P3HT BHJ cells.
- Zhang, Youdi,Chen, Lingcheng,Zhang, Kaichen,Wang, Helin,Xiao, Yi
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p. 10170 - 10178
(2014/08/18)
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- The extension of conjugated system in pyridyl-substituted monoazatriphenylenes for the tuning of photophysical properties
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We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels-Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.
- Kopchuk,Khasanov,Kovalev,Zyryanov,Kim,Nikonov,Rusinov,Chupakhin
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p. 871 - 879
(2014/11/08)
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- The extension of conjugated system in pyridyl-substituted monoazatriphenylenes for the tuning of photophysical properties
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We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels-Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.
- Kopchuk,Khasanov,Kovalev,Zyryanov,Kim,Nikonov,Rusinov,Chupakhin
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p. 871 - 879
(2015/09/28)
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- METAL COMPLEXES WITH DIBENZO[F,H]QUINOXALINES
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This invention relates to electroluminescent metal complexes of the formula electronic devices comprising the metal complexes and their use in electronic devices, especially organic light emitting diodes (OLEDs). The metal complexes of formula (I) show hi
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Page/Page column 42-43
(2013/07/25)
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- Novel thieno-imidazole based probe for colorimetric detection of Hg 2+ and fluorescence turn-on response of Zn2+
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Novel thieno-imidazole based polymer P showed both colorimetric and ratiometric detections of Hg2+ as well as fluorometric detection of Zn2+ via fluorescence turn-on response with augmented lifetime. Its model polymer M did not show any such sensing capability under similar conditions, which further confirmed the unique sensitivity of P toward Hg 2+ and Zn2+ via the chelation of metal ions to both "S" and "N" heteroatoms.
- Satapathy, Rudrakanta,Wu, Yen-Hsing,Lin, Hong-Cheu
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supporting information; experimental part
p. 2564 - 2567
(2012/07/14)
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- Effect of conjugated core building block dibenzo[a,c]phenazine unit on π-conjugated electrochromic polymers: Red-shifted absorption
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A comparative investigation was undertaken for the electrosynthesis and electrochemical properties of three different electroactive polymers having a conjugated core building block, dibenzo[a,c]phenazine. A series of monomers has been synthesized as regards to thiophene based units; thiophene, 3-hexyl thiophene, and 3,4-ethylenedioxythiophene. The effects of different donor substituents on the polymers' electrochemical properties were examined by cyclic voltammetry. Introducing highly electron-donating (ethylene dioxy) group to the monomer enables solubility while also lowering the oxidation potential. The planarity of the monomer unit enhances π-stacking and consequently lowering the Eg from 2.4 eV (PHTP) to 1.7 (PTBP). Cyclic voltammetry and spectroelectrochemical measurements revealed that 2,7-bis(4-hexylthiophen-2-yl) dibenzo[a,c]phenazine (HTP) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5- yl)dibenzo[a,c]phenazine (TBP) possessed electrochromic behavior. The colorimetry analysis revealed that while PTBP have a color change from red to blue, PHTP has yellow color at neutral state and blue color at oxidized state. Hence the presence of the phenazine derivative as the acceptor unit causes a red shift in the polymers' absorption to have a blue color.
- Unver, Elif Kose,Tarkuc, Simge,Udum, Yasemin Arslan,Tanyeli, Cihangir,Toppare, Levent
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experimental part
p. 1714 - 1720
(2011/03/22)
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- Synthesis of electron-accepting polymers containing phenanthra-9,10-quinone units
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Polymers containing 9,10-phenanthraquinone moieties as part of an extended π-electron system have been prepared by Suzuki couplings between 2,7- or 3,6-dibromophenanthraquinone and 9,9-dioctylfluorene-2,7-diboronic acid bispinacol ester. Closely related model compounds were prepared similarly. All the products were characterised by FT-IR, 1H NMR and UV-vis/fluorescence spectroscopy and, where relevant, mass spectrometry. Cyclic voltammetry measurements indicate that these materials display electron affinities of up to 4.0 eV. This value is one of the highest reported for conjugated polymers.
- Gautrot, Julien E.,Hodge, Philip,Helliwell, Madeleine,Raftery, James,Cupertino, Domenico
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experimental part
p. 4148 - 4156
(2010/05/02)
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- Facile synthesis of 9,10-diarylphenanthrenes and poly(9,10- diarylphenanthrene)s
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One-pot reduction of 9,10-diaryl-9,10-dihydrophenanthrene-9,10-diols to 9,10-diarylphenanthrenes was achieved with Zn/H+ in acetic acid. Accordingly, various novel phenanthrenes and polyphenanthrenes with efficient blue emission were easily synthesized.
- He, Bo,Tian, Hongkun,Geng, Yanhou,Wang, Fosong,Mllen, Klaus
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supporting information; experimental part
p. 773 - 776
(2009/04/06)
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- PHENANTHRENE COMPOUNDS
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A phenanthrene compound represented by the formula (I): in which, R1, R2, R3, R4, R5, R6, R7, and R8 are identical or different and may each be hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, or a conjugated group. The phenanthrene compound has a polycyclic structure and semiconductor properties including electron transfer, electroluminescence, and photoluminescence.
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Page/Page column 5
(2008/06/13)
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