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Small Heterocyclic D‐π‐D‐π‐A Push‐Pull Molecules with Complex Electron Donors
Author(s) -
Kulhánek Jiří,
Pytela Oldřich,
Bureš Filip,
Klikar Milan
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100137
Subject(s) - chemistry , moiety , linker , furan , thiophene , molecule , chromophore , cyclic voltammetry , phenylene , stereochemistry , photochemistry , electrochemistry , organic chemistry , polymer , electrode , computer science , operating system
Abstract A large series of small push‐pull chromophores based on electron‐withdrawing N , N '‐dibutylthiobarbituric acid has been designed and successfully synthesized. The electron donating part involves common mesomeric donors such as methoxy, N , N ‐dimethylamino, N , N ‐diphenylamino, and piperidin‐1‐yl groups. Five‐membered heteroaromatics, namely thiophene, N ‐methylpyrrole, and furan have been employed as electron rich π‐linkers and auxiliary donors. Structural analogues bearing aromatic 1,4‐phenylene linker were also synthesized for comparison. Fundamental thermal and optoelectronic properties were studied by differential scanning calorimetry, cyclic voltammetry, and absorption spectroscopy. Thorough structure‐property relationships were elucidated, focusing mostly on type of the used π‐linker and donor. All experimental conclusions are corroborated by theoretical calculations. The study has shown that a complex donor moiety may be built by properly combining mesomeric and auxiliary donors. Whereas strong mesomeric donor (amino) suppresses the donating effect of auxiliary donors/π‐linkers, a combination of weak donor (methoxy) appended at a five‐membered heterocycle pronounces the donating ability of the latter.