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We have examined the synthesis of cyclic oligomers with pendant norbornadiene (NBD) moieties based on the calixarenes [p-tert-butylcalix[8]arene (BCA), p-methylcalix[6]arene (MCA), calix[4]resorcinarene (CRA), 2,8,14,20-tetradecylcalix[4]resorcinarene (CRA10), and 2,8,14,20-tetrakis(p-hydroxyphenyl)calix[4]resorcinarene (CRAph)]. The photochemical valence isomerization of the obtained calixarene derivatives containing NBD moieties proceeded very smoothly to afford the corresponding quadricyclane (QC) moieties, and it was found that the large refractive-index changes (Δn’s = 0.028–0.061) before and after photo-isomerization.
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Kudo et al. (2004) studied this question.
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