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Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s
Chirality ( IF 2.8 ) Pub Date : 2020-11-15 , DOI: 10.1002/chir.23282 Martina Marinelli 1 , Luigi Angiolini 1 , Massimiliano Lanzi 1 , Francesca Di Maria 2 , Elisabetta Salatelli 1
Chirality ( IF 2.8 ) Pub Date : 2020-11-15 , DOI: 10.1002/chir.23282 Martina Marinelli 1 , Luigi Angiolini 1 , Massimiliano Lanzi 1 , Francesca Di Maria 2 , Elisabetta Salatelli 1
Affiliation
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Novel optically active oligothiophenes bearing electron‐donating chiral side chains have been prepared by synthetic methods suitable to achieve regioregular head‐to‐tail and head‐to‐head/tail‐to‐tail derivatives. In particular, the chiral (S)‐(2‐methyl)butyl moiety was linked at position 3 of the thiophene ring through heteroatoms, such as S or O, to evaluate its effect on the macro molecular aggregation and, consequently, on the chiroptical properties of the material in the solid state. The materials have been fully characterized and investigated by optical and chiroptical methods upon aggregation both from the solution and as cast films. Compared with the related head‐to‐tail and head‐to‐head/tail‐to‐tail poly(3‐alkyl)thiophene derivatives, with the same optically active moiety directly linked to the ring and possessing a higher polymerization degree, the chiroptical properties of the newly synthesized oligomers were significant, or even better, and provided insight into the role of intrachain–interchain interactions between the heteroatom and the thienyl sulfur atom.
中文翻译：
区域规整性和杂原子作用对低聚（杂烷基噻吩）手性行为的影响
通过适合实现区域规则的头对尾和头对头/尾对尾衍生物的合成方法，已经制备了具有给电子手性侧链的新型光学活性低聚噻吩。特别是，手性（S)-(2-甲基)丁基部分通过杂原子（如 S 或 O）连接在噻吩环的 3 位，以评估其对大分子聚集的影响，从而对固体中材料的手性光学性质进行评估状态。在从溶液和流延膜聚集后，这些材料已经通过光学和手性光学方法进行了充分的表征和研究。与相关的头对尾和头对头/尾对尾聚（3-烷基）噻吩衍生物相比，具有相同的光学活性部分直接连接到环并具有更高的聚合度，手性新合成的低聚物的性质很重要，甚至更好，并提供了对杂原子和噻吩硫原子之间链内-链间相互作用作用的洞察。
更新日期：2020-11-21
中文翻译：
区域规整性和杂原子作用对低聚（杂烷基噻吩）手性行为的影响
通过适合实现区域规则的头对尾和头对头/尾对尾衍生物的合成方法，已经制备了具有给电子手性侧链的新型光学活性低聚噻吩。特别是，手性（S)-(2-甲基)丁基部分通过杂原子（如 S 或 O）连接在噻吩环的 3 位，以评估其对大分子聚集的影响，从而对固体中材料的手性光学性质进行评估状态。在从溶液和流延膜聚集后，这些材料已经通过光学和手性光学方法进行了充分的表征和研究。与相关的头对尾和头对头/尾对尾聚（3-烷基）噻吩衍生物相比，具有相同的光学活性部分直接连接到环并具有更高的聚合度，手性新合成的低聚物的性质很重要，甚至更好，并提供了对杂原子和噻吩硫原子之间链内-链间相互作用作用的洞察。
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