Microbiology, Bioorganic and Macromolecular Chemistry (MBMC) Unit, Faculty of Pharmacy, Université Libre de Bruxelles, 1050 Brussels, Belgium.
XStruct, Department of Chemistry, Ghent University, Krijgslaan 281-S3, 9000 Ghent, Belgium.
Int J Mol Sci. 2023 Jul 5;24(13):11127. doi: 10.3390/ijms241311127.
A supramolecular self-assembly of semiconducting polymers and small molecules plays an important role in charge transportation, performance, and lifetime of an optoelectronic device. Tremendous efforts have been put into the strategies to self-organize these materials. In this regard, here, we present the self-organization of terthiophene and its methyl alcohol derivative with 4,4'-bipyridine (44BiPy). An unexpected 2D layered organization of 5,5″-dimethyl-2,2':5',2″-terthiophene (DM3T) and 44BiPy was obtained and analyzed. Single-crystal X-ray diffraction analysis revealed that DM3T and 44BiPy consist of stacked, almost independent, infinite 2D layers while held together by weak hydrogen bonds. In addition to this peculiar supramolecular arrangement of these compounds, the investigation of their photophysical properties showed strong fluorescence quenching of DM3T by 44BiPy in the solid state, suggesting an efficient charge transfer. On the other hand, the methyl alcohol derivative of terthiophene, DM3TMeOH, organized in a closed cyclic motif with 44BiPy via hydrogen bonds.
半导体聚合物和小分子的超分子自组装在光电设备的电荷输运、性能和寿命中起着重要作用。人们已经投入了大量的努力来研究这些材料的自组织策略。在这方面，我们展示了噻吩及其甲醇衍生物与 4,4'-联吡啶（44BiPy）的自组织。我们得到并分析了 5,5″-二甲基-2,2':5',2″-噻吩（DM3T）和 44BiPy 的二维层状结构。单晶 X 射线衍射分析表明，DM3T 和 44BiPy 由堆叠的、几乎独立的无限二维层组成，同时通过弱氢键结合在一起。除了这些化合物的特殊超分子排列外，对其光物理性质的研究表明，DM3T 在固态下被 44BiPy 强烈荧光猝灭，表明存在有效的电荷转移。另一方面，噻吩的甲醇衍生物 DM3TMeOH 通过氢键与 44BiPy 形成闭合环状结构。
