Push-pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes
TETRAHEDRON, cilt.72, sa.9, ss.1213-1224, 2016 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 72 Sayı: 9
- Basım Tarihi: 2016
- Doi Numarası: 10.1016/j.tet.2016.01.017
- Dergi Adı: TETRAHEDRON
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1213-1224
- Anahtar Kelimeler: [2+2] Cycloaddition, Fluoranil, Chloranil, Quinones, Push-pull chromophores, INTRAMOLECULAR CHARGE-TRANSFER, PHOTOINDUCED ELECTRON-TRANSFER, PORPHYRIN-QUINONE CYCLOPHANES, DONOR-ACCEPTOR SYSTEMS, DIELS-ALDER REACTION, PLANT PHOTOSYSTEM-I, TRANSFER COMPLEXES, CRYSTAL-STRUCTURE, ARTIFICIAL PHOTOSYNTHESIS, OPTOELECTRONIC PROPERTIES
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
A series of new push-pull chromophores were synthesized from electron-rich 4-(N,N-dialkylanilino) acetylenes and 2,3,5,6-tetrahalo-1,4-benzoquinones. The reactivity of the latter differs substantially from that of the previously investigated 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The transformation with fluoranil gave orange-colored, bis-donor-substituted chromophores with a tricyclic, cyclobutene-fused dihydrobenzofuranone core. In contrast, the reaction with chioranil yielded mono donor-substituted, blue 1,4-benzoquinone-based chromophores, which were further reacted with tertiary amines to form bis-donor-substituted push-pull systems. The structures of the new chromophores were confirmed by X-ray analysis, and mechanisms for their formation are proposed. They feature intense intramolecular charge-transfer bands in the visible region, and their optoelectronic properties were investigated by UV/Vis spectroscopy, electrochemistry, and computational analysis. (C) 2016 Elsevier Ltd. All rights reserved.