122107-04-4Relevant articles and documents
Synthesis of thiophene-based π-conjugated polymers containing oxadiazole or thiadiazole moieties and their application to organic photovoltaics
Higashihara, Tomoya,Wu, Hung-Chin,Mizobe, Tetsunari,Lu, Chien,Ueda, Mitsuru,Chen, Wen-Chang
, p. 9046 - 9055 (2012)
We report the synthesis, properties, and photovoltaic applications of new π-conjugated polymers having thiophene, 3,4-dihexylthiophene, and 1,3,4-oxadiazole (OXD) or 1,3,4-thiadiazole (TD) units in the main chain, denoted as P1 and P2. They were synthesized by the Stille coupling reaction of 2,5-bis(trimethylstannyl)thiophene and the corresponding monomers of 2,5-bis(5′-bromo-3′,4′-dihexylthien-2′-yl)-1,3, 4-oxadiazole or 2,5-bis(5′-bromo-3′,4′-dihexylthien-2′- yl)-1,3,4-thiadiazole, respectively. The experimental results indicated that the introduction of an electron-accepting moiety of OXD or TD lowered the highest occupied molecular orbital (HOMO) energy levels, resulting in the higher the open-circuit voltage (Voc) values of polymer solar cells (PSCs). Indeed, the PSCs of P1 and P2 showed high Voc values in the range 0.80-0.90 V. The highest field-effect transistor (FET) mobilities of P1 and P2 with the OXD and TD moieties, respectively, were 1.41 × 10-3 and 8.81 × 10-2 cm2 V-1 s-1. The higher mobility of P2 was related to its orderly nanofibrillar structure, as evidenced from the TEM images. Moreover, the higher absorption coefficient and smaller band gap of P2 provided a more efficient light-harvesting ability. The power conversion efficiency (PCE) of the PSC based on P2:PCBM = 1:1 (w/w) reached 3.04% with a short-circuit current density (Jsc) value of 6.60 mA/cm2, a Voc value of 0.80 V, and a fill factor (FF) value of 0.576 during the illumination of AM 1.5, 100 mW/cm2. In comparison, the parent PDHBT without the electron-accepting moiety exhibited an inferior device performance (FET mobility = 2.10 × 10-4 cm 2 V-1 s-1 and PCE = 1.91%). The experimental results demonstrated that incorporating the electron-acceptor moiety into the polythiophene backbone could enhance the device performance due to the low-lying HOMO levels, compact packing structure, and high charge carrier mobility. This is the first report for the achievement of PCE > 3% using PSCs based on polythiophenes having TD units in the main chain.
Synthesis and photoinduced intramolecular processes of fulleropyrrolidine- oligothienylenevinylene-ferrocene triads
Oswald, Frederic,Islam, D.-M. Shafiqul,Araki, Yasuyuki,Troiani, Vincent,De La Cruz, Pilar,Moreno, Andres,Ito, Osamu,Langa, Fernando
, p. 3924 - 3933 (2007)
Two new triads based on N-methylfulleropyrolidine, oligothienylenevinylenes (nTV) and ferrocene (Fc), namely C60-nTV-Fc (n = 2, 4) have been synthesized. A HOMOLUMO gap as low as 1.09-1.11 eV was experimentally determined by cyclic voltammetry. In both polar and nonpolar solvents, photoinduced charge-separation (CS) processes in C60-nTV-Fc predominantly take place from the singlet excited states of C60 and nTV; this result was indicated by steady and time-resolved emission spectroscopy. In the case of C60-4TV-Fc, the CS state was indicated by the nanosecond transient absorption spectra. In C60-2TV-Fc, although the CS process was also confirmed by the fluorescence quenching in nonpolar and polar solvents, the lifetimes of the CS states were shorter than those of C60-4TV-Fc. It was revealed that the introduction of Fc donor moiety at the end of the longer nTV chain in the C60-nTV dyad systems effectively increases the CS efficiency and the lifetimes of CS states.
Tuning of the photophysical and electrochemical properties of symmetric and asymmetric conjugated thiophenoazomethines
Liu, Shengzhen,Wu, Ti,Zhu, Qi,Pu, Jialing,Chen, Guangxue,Zhang, Weimin,Li, Zhongxiao
, p. 12779 - 12784 (2018/04/16)
A synthetic route towards symmetric and asymmetric thiophenoazomethines was accomplished by reaction of the readily available amine with various aldehydes. Investigation of a series of thiophenoazomethines obtained by this method indicates that the terminal groups and the degree of conjugation have a great effect on the electronic absorption and energy levels of the conjugated compounds, particularly the effect of terminal groups. The terminal withdrawing and donating groups of thiophenoazomethines led to the formation of an electronic push-pull, push-push and pull-pull system, which can perturb the electronic transitions between the ground and excited states. The flexible chain substituents on the thiophene units, which improve its solubility, also result in bathochromic absorption, but have limited effect on the energy level.
Azomethine-bridged thiophene compounds and preparation method thereof
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Paragraph 0066; 0067, (2017/09/02)
The invention relates to azomethine-bridged thiophene compounds and a preparation method thereof. The structural general formula of the compounds is shown in the description. In the structural general formula, R1 is linear alkyl, branch alkyl or a linear ester group; R2, R3 and R4 are electrophilic groups or hydrogen, at least one of R2, R3 and R4 has an electrophilic group and the electrophilic group contains cyano, halogen or trifluoromethyl; X is a carbon atom, Y is a nitrogen atom, or X is a nitrogen atom and Y is a carbon atom; and m is an integer of 0-1. The preparation method is capable of preparing the azomethine-bridged thiophene compounds with symmetric structures or asymmetric structures. A thiophene derivative is employed as a raw material, an amino-substituted thiophene derivative and a phenol-substituted thiophene derivative are subjected to a dehydration condensation reaction to obtain a target product, and the yield reaches 40% or more. The obtained azomethine-bridged thiophene compounds can be widely applied to organic light emitting diodes, field-effect tubes, flexible active matrix display, organic radio frequency electronic trademarks, organic sensors/storers, organic functional plastics, electronic paper and solar cells.
