Grucela-Zajac Marzena, Bijak Katarzyna, Kula Slawomir, Filapek Michal, Wiacek Malgorzata, Janeczek Henryk, Skorka Lukasz, Gasiorowski Jacek, Hingerl Kurt, Sariciftci Niyazi Serdar, Nosidlak Natalia, Lewinska Gabriela, Sanetra Jerzy, Schab-Balcerzak Ewa
Institute of Chemistry, University of Silesia , 9 Szkolna Street, 40-006 Katowice, Poland.
Centre of Polymer and Carbon Materials, Polish Academy of Sciences , 34 M. Curie-Sklodowska Street, 41-819 Zabrze, Poland.
J Phys Chem C Nanomater Interfaces. 2014 Jun 19;118(24):13070-13086. doi: 10.1021/jp501168b. Epub 2014 May 21.
New symmetrical arylene bisimide derivatives formed by using electron-donating-electron-accepting systems were synthesized. They consist of a phthalic diimide or naphthalenediimide core and imine linkages and are end-capped with thiophene, bithiophene, and (ethylenedioxy)thiophene units. Moreover, polymers were obtained from a new diamine, ,'-bis(5-aminonaphthalenyl)naphthalene-1,4,5,8-dicarboximide and 2,5-thiophenedicarboxaldehyde or 2,2'-bithiophene-5,5'-dicarboxaldehyde. The prepared azomethine diimides exhibited glass-forming properties. The obtained compounds emitted blue light with the emission maximum at 470 nm. The value of the absorption coefficient was determined as a function of the photon energy using spectroscopic ellipsometry. All compounds are electrochemically active and undergo reversible electrochemical reduction and irreversible oxidation processes as was found in cyclic voltammetry and differential pulse voltammetry (DPV) studies. They exhibited a low electrochemically (DPV) calculated energy band gap () from 1.14 to 1.70 eV. The highest occupied molecular orbital and lowest unoccupied molecular orbital levels and were additionally calculated theoretically by density functional theory at the B3LYP/6-31G(d,p) level. The photovoltaic properties of two model compounds as the active layer in organic solar cells in the configuration indium tin oxide/poly(3,4-(ethylenedioxy)thiophene):poly(styrenesulfonate)/active layer/Al under an illumination of 1.3 mW/cm were studied. The device comprising poly(3-hexylthiophene) with the compound end-capped with bithiophene rings showed the highest value of (above 1 V). The conversion efficiency of the fabricated solar cell was in the range of 0.69-0.90%.
通过使用供电子-吸电子体系合成了新型对称亚芳基双酰亚胺衍生物。它们由邻苯二甲酰亚胺或萘二甲酰亚胺核心以及亚胺键组成，并以噻吩、联噻吩和（乙撑二氧基）噻吩单元封端。此外，由新型二胺、1,4,5,8-萘四甲酸二酐与2,5-噻吩二甲醛或2,2'-联噻吩-5,5'-二甲醛反应得到了聚合物。所制备的甲亚胺二酰亚胺表现出玻璃形成特性。所得到的化合物发射蓝光，发射最大值在470nm处。使用光谱椭偏仪测定了吸收系数随光子能量的变化函数。所有化合物都具有电化学活性，在循环伏安法和差分脉冲伏安法（DPV）研究中发现它们经历可逆的电化学还原和不可逆的氧化过程。它们的电化学（DPV）计算能带隙（Eg）较低，在1.1
