Krittaphat WongmaNantiya BunbamrungTienthong ThongpanchangMahidol University2018-12-112019-03-142018-12-112019-03-142016-03-24Tetrahedron. Vol.72, No.12 (2016), 1533-154014645416004040202-s2.0-84958885578https://repository.li.mahidol.ac.th/handle/123456789/43111© 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.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1016/j.tet.2016.02.001