Pyridalthiadiazole acceptor-functionalized triarylboranes with multi-responsive optoelectronic characteristics

Chemical Science
Xiaodong YinFrieder Jäkle

Abstract

A new class of Ar2B-π-A dyads and A-π-B(Ar)-π-A triads that feature strong organic acceptor moieties (A = pyridalthiadiazole, PT) attached to a central triarylborane were synthesized via Stille cross-coupling of ArB(Th-SnMe3)2 (Th = thiophenediyl, Ar = 2,4,6-tri-tert-butylphenyl (Mes*) or 2,4,6-tris(trifluoromethylphenyl) (FMes)) with one or two equivalents of dibromopyridalthiadiazole. Single-crystal X-ray crystallography data for the triad Mes*B(Th-PT-Br)2 indicate a highly coplanar conformation, which is ideal for extended π-conjugation and favors intermolecular π-stacking. Despite the presence of Br substituents, these compounds exhibit strong photoluminescence in THF solution with quantum yields reaching up to 52%. Further extension of conjugation by coupling with 2-hexylthiophene leads to additional bathochromic shifts to give a highly soluble and strongly red-emissive material. All these compounds undergo facile reduction, first of the PT substituents and then at more negative potentials for the borane moiety. Upon chemical reduction with in THF, an intramolecular charge transfer (ICT) pathway from the reduced PT moieties to boron is enabled and this results in a change of the color to blue. Theoretical calculations reve...Continue Reading

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Citations

Jun 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Frank PammerAndreas Orthaber
Nov 7, 2019·Chemistry : a European Journal·Yingjian YuLixiang Wang
Jun 1, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Nicolas A RienschHolger Helten
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Jan 21, 2021·Chemical Communications : Chem Comm·Yohei AdachiJoji Ohshita
Dec 15, 2020·Chemistry : a European Journal·Yohei AdachiJoji Ohshita
Jan 15, 2021·Chemistry : a European Journal·Sarina M BergerTodd B Marder
Oct 3, 2019·Journal of the American Chemical Society·Yang MinJun Liu
Feb 11, 2020·Inorganic Chemistry·Sudhakar PagidiPakkirisamy Thilagar
Sep 25, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Min Wang, Cui-Hua Zhao

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Methods Mentioned

BETA
column chromatography
X-ray
NMR

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