18791-78-1Relevant articles and documents
Nanotubular structures through templateless electropolymerization using thieno[3,4-b]thiophene derivatives with different substituents and water content
Sane, Omar,Diouf, Alioune,Pan, Miaobo,Morán Cruz, Gabriela,Savina,Méallet-Renault, Rachel,Dieng, Samba Yandé,Amigoni,Guittard, Frédéric,Darmanin, Thierry
, (2019)
Here, we report a strategy to prepare controllable nanotubular structures using a templateless electropolymerization process in organic solvent (CH2Cl2) and without surfactant. We use thieno [3,4-b]thiophene derivatives with various substituents including hydrocarbon chains, fluorocarbon chains and aromatic groups of various size. The influence of the water content (CH2Cl2 + H2O) in also studied in order to release in-situ a higher amount of gas bubbles (O2 and/or H2). The best results are obtained with the pyrene substituent, which lead to highly densely packed nanotubular structures while the water content allows to highly increase their porosity, changing the resulting surface morphology from tree-like to coral-like structure. This is probably due to both high π-stacking interaction of pyrene and its polymerization capacity in the same potential range. This change also induces an increase in surface hydrophilicity because the water highly penetrates these porous structures. Moreover, both the poly (thieno [3,4-b]thiophene) polymers and the substituents participate to the film fluorescence while the nanostructures seem to amplify their intensity. Such surfaces are extremely interesting for potential applications in sensors or in water harvesting systems.
Isomerizing thieno[3,4-: B] thiophene-based near-infrared non-fullerene acceptors towards efficient organic solar cells
Kong, Lingwei,Liu, Feng,Shan, Tong,Zhang, Yi,Zhang, Zeqi,Zhong, Hongliang,Zhu, Lei
supporting information, p. 4357 - 4364 (2020/04/15)
With the rapid growth in the requirement for emerging photovoltaic technology like semitransparent solar cells applied for integrated smart windows, there is an urgent need to develop near-infrared (NIR) non-fullerene acceptors (NFAs). To address this issue, thieno[3,4-b]thiophene (TT), which has a stable quinoid structure to minimize the energy difference between two resonance structures corresponding to the band gap, is introduced into the push-pull molecular architecture as a bridge unit to narrow the band gap of the derived acceptors. Due to the different linkage positions (4-or 6-position) of asymmetric TT, these acceptors are classified into two types of isomers, namely 4TIC, 4T4F, 6TIC and 6T4F, of which all have strong absorption in the NIR range. By incorporation with polymer donor PTB7-Th, the devices based on 6-position isomers exhibit superior photovoltaic performance, wherein a champion device based on 6T4F is obtained with a power conversion efficiency of 10.74%. With detailed investigations on inherent optoelectronic properties as well as structural and morphological variation, this performance diversity induced by isomerism is determined by the evident difference in the packing order, which will impact the charge mobility and fill factor. This work presents a class of high-performance NIR acceptors in which the regioisomeric backbone will significantly impact the optoelectronic properties.
Synthesis of Unsymmetric Monosubstituted and Disubstituted Dinaphthothiophenes
Throgmorton, John C.,Chintala, Satyanarayana M.,McCulla, Ryan D.
supporting information, p. 3682 - 3688 (2017/10/09)
Dinaphthothiophenes (DNTs) are a class of compounds with potential uses in organic semiconductors and the synthesis of unsymmetric catalysts. Symmetrical or asymmetrical addition of functional groups to the DNT structure may be desired for steric bulk in binaphthyl catalyst synthesis or tuning the electronic properties of semiconductors. Thus, versatility of functional group addition is a great asset in DNT synthesis. Until now, no versatile and concise methods for the synthesis of unsymmetrically substituted DNTs have been reported. Herein, we report three synthetic routes for the creation of three different classes of DNTs. Each route involves the successive addition of two functionalized styryl groups to a thiophene ring, followed by a photocyclization to form the desired asymmetric DNT. Various novel unsymmetrically monosubstituted and disubstituted dinaphtho[2,1-b:1′,2′-d]thiophenes, dinaphtho[1,2-b:1′,2′-d]thiophenes, and dinaphtho[1,2-b:2′,1′-d]thiophenes were synthesized from 2-bromothiophene,2,4-dibromothiophene, and 3,4-dibromothiophene in three or four steps. These methods can be used to synthesize a wide variety of unsymmetrically functionalized DNTs.
