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Sharp Turns and Fluorescent Repeats: Modular Construction and Shape‐Dependent Electronic Properties of π‐Conjugated Chain Molecules
Author(s) -
Lee Milim,
Kang Sukil,
Song Sungmin,
Kim Hongsik,
Lee Dongwhan
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000818
Subject(s) - conjugated system , molecule , modular design , benzene , context (archaeology) , nitro , fluorescence , chemistry , chain (unit) , ring (chemistry) , combinatorial chemistry , series (stratigraphy) , substituent , materials science , stereochemistry , computer science , physics , polymer , organic chemistry , quantum mechanics , paleontology , alkyl , biology , operating system
In search of the design rules for structural ordering of open‐chain molecules, we have built a series of zig‐zag shaped π‐conjugated structures with ring‐fused heteroaromatics as sharp turns and tolane‐based linear fragments as light‐emitting units. Using only a finite number of common building blocks, an efficient “double‐elongation” strategy was implemented to construct a series of π‐conjugated oligomers with precise length control (55–89 % yields). Our approach takes advantage of the modular nature of the bis(triazolo)benzene synthesis and the masked reactivity of the nitro group. A combination of photophysical and DFT computational studies revealed that the bis(triazolo)benzene–tolane repeat units behave as electronically decoupled light‐absorbing/emitting units (λ max,em = 408–422 nm; Φ F = 20–25 % in THF). Such context‐independent photophysical properties promise their potential applications in chemical sensing and switching.