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Title: Synthesis of bridged biarylbisquinones and effects of biaryl dihedral angles on photo- and electro-chemical properties
Authors: Krittaphat Wongma
Nantiya Bunbamrung
Tienthong Thongpanchang
Mahidol University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry
Issue Date: 24-Mar-2016
Citation: Tetrahedron. Vol.72, No.12 (2016), 1533-1540
Abstract: © 2016 Elsevier Ltd. All rights reserved. A series of bridged biarylbisquinones, QBINOLs 1-4, and their corresponding monomers, QNaphs 5-6, were designed to demonstrate the influence of biaryl conformation on the photo- and electro-chemical properties of the molecules. All target compounds were synthesized from the Diels-Alder reaction between silyl enol ethers of the corresponding naphthyl or binaphthyl derivatives and p-benzoquinone. Addition of an OMe auxochrome or formation of the dimeric structures affect the absorption spectra and the energy band gap (Eg), but not the reduction potentials of the molecules. Narrowing the dihedral angles of the QBINOLs by shortening methylene bridges limited the contribution of bridging OR auxochromes and therefore resulted in lower HOMO levels and larger Eg.
ISSN: 14645416
Appears in Collections:Scopus 2016-2017

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