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Alkoxy‐Substituted Hexastyrylbenzenes
Author(s) -
Meier Herbert,
Holst Hans Christof
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303030
Subject(s) - chemistry , alkoxy group , chromophore , benzene , wittig reaction , medicinal chemistry , ring (chemistry) , absorption (acoustics) , heck reaction , stereochemistry , palladium , photochemistry , organic chemistry , alkyl , catalysis , physics , acoustics
Abstract Star‐shaped compounds 2a–e with a central benzene ring and six p ‐substituted, ( E )‐configured styryl groups have been prepared by a sequence of three‐fold Heck and three‐fold Wittig–Horner reactions. Alkoxy chains (OC 3 H 7 , OC 6 H 13 , OC 10 H 21 , OC 12 H 25 ) on all six arms guarantee a good solubility of 2a–d , whereas the alternating hexyloxy and cyano substitution in 2e leads to an almost insoluble push‐pull system. Irradiation into the long‐wavelength absorption of 2a–d (with λ max values of 341–342 nm) results in a statistical photocross‐linking, which is characterized by the complete degradation of all stilbene chromophores.