π-Extension of the Tribenzotriquinacene Framework: Efficient Vinylene and Arylene Bay Bridging Based on a New C 3 -Symmetric Key Derivative.

Autor: Wang HZ; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR., Hung TY; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR., Ip HW; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR., Lee MK; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR., Sun XQ; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR., Kuck D; Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615, Bielefeld, Germany., Chow HF; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Jun 27; Vol. 29 (36), pp. e202300793. Date of Electronic Publication: 2023 May 03.
DOI: 10.1002/chem.202300793
Abstrakt: 1,5,9-Tribromo-2,3,6,7,10,11-hexamethoxy-4b 1 -methyltribenzotriquinacene, a C 3 -symmetric TBTQ derivative, can be prepared conveniently and with high regioselectivity from readily available starting materials. It is a versatile key compound for the synthesis of other chiral 1,5,9-trifunctionalized TBTQ derivatives and π-extended congeners in which the bays of the TBTQ skeleton are bridged by vinylene and 1,2-arylene units. X-ray crystal structure analysis and UV-vis spectroscopy show that vinylene bay-bridging enables better π-conjugation with the arene rings of the TBTQ core than 1,2-arylene bay-bridging does.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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