Thermally reversible photochromic behaviour of new naphthopyrans involving an intramolecular [2+2] cyclization reaction
作者： Paulo J. Coelho , Luís M. Carvalho , Gaston Vermeersch , Stephanie Delbaere
DOI: 10.1016/J.TET.2009.04.070
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摘要: New 4-(2,2-diphenylethenyl)naphthopyrans were synthesized and their photochromic behaviour in solution studied under continuous UV light irradiation conditions. Although only one coloured photoproduct was expected to be formed, due the naphthopyran substitution pattern, NMR analysis on degassed irradiated solutions, performed at low temperature, showed formation of different compounds. Among them, main product is formed through an intramolecular [2+2] cyclization reaction show thermally reversible properties.
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sci-hub.se 参考文章(16)
John C. Crano, Robert J. Guglielmetti, Main photochromic families Plenum Press. ,(1999)
M. Manuel Oliveira, Maria A. Salvador, Stéphanie Delbaere, Jérôme Berthet, G. Vermeersch, J.C. Micheau, Paulo J. Coelho, Luís M. Carvalho, Remarkable thermally stable open forms of photochromic new N-substituted benzopyranocarbazoles Journal of Photochemistry and Photobiology A-chemistry. ,vol. 198, pp. 242- 249 ,(2008) , 10.1016/J.JPHOTOCHEM.2008.03.019
Paulo J. Coelho, Maria A. Salvador, M. Manuel Oliveira, Luis M. Carvalho, Photochemical and thermal behaviour of new photochromic indeno-fused naphthopyrans Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 172, pp. 300- 307 ,(2005) , 10.1016/J.JPHOTOCHEM.2004.12.019
Christopher D. Gabbutt, B. Mark Heron, Suresh B. Kolla, Colin Kilner, Simon J. Coles, Peter N. Horton, Michael B. Hursthouse, Ring contraction during the 6π-electrocyclisation of naphthopyran valence tautomers Organic and Biomolecular Chemistry. ,vol. 6, pp. 3096- 3104 ,(2008) , 10.1039/B807744D
Christopher D. Gabbutt, B. Mark Heron, Alicia C. Instone, The synthesis and electronic absorption spectra of 3-phenyl-3(4-pyrrolidino-2-substituted phenyl)-3H-naphtho[2,1-b]pyrans: further exploration of the ortho substituent effect Tetrahedron. ,vol. 62, pp. 737- 745 ,(2006) , 10.1016/J.TET.2005.09.143
Wilasinee Sriprom, Marjorie Néel, Christopher D. Gabbutt, B. Mark Heron, Sébastien Perrier, Tuning the color switching of naphthopyrans via the control of polymeric architectures Journal of Materials Chemistry. ,vol. 17, pp. 1885- 1893 ,(2007) , 10.1039/B617865K
J??r??me Berthet, St??phanie Delbaere, David Levi, Andr?? Samat, Robert Guglielmetti, Gaston Vermeersch, Studies of polyphotochromic behaviour of supermolecules by NMR spectroscopy. Part 2. A bis-[3H]naphthopyran with a (Z)-ethenic bridge between each moietyPart 1 is indicated in ref. 5. Photochemical and Photobiological Sciences. ,vol. 1, pp. 665- 672 ,(2002) , 10.1039/B203014D
Stéphanie Delbaere, Barbara Luccioni-Houze, Christophe Bochu, Yannick Teral, Mylène Campredon, Gaston Vermeersch, Kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy Journal of The Chemical Society-perkin Transactions 1. pp. 1153- 1158 ,(1998) , 10.1039/A800906F
Nino Malic, Jonathan A. Campbell, Richard A. Evans, Superior Photochromic Performance of Naphthopyrans in a Rigid Host Matrix Using Polymer Conjugation: Fast, Dark, and Tunable Macromolecules. ,vol. 41, pp. 1206- 1214 ,(2008) , 10.1021/MA071792L
Paulo J Coelho, Maria A Salvador, M.Manuel Oliveira, Luis M Carvalho, The effect of a sulphur bridge on the photochromic properties of indeno-fused naphthopyrans Tetrahedron. ,vol. 60, pp. 2593- 2599 ,(2004) , 10.1016/J.TET.2004.01.034