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Synthesis, Gelation Properties and Photopolymerization of Macrocyclic Diacetylenedicarboxamides Derived from L ‐Glutamic Acid and trans ‐1,4‐Cyclohexanediol
Author(s) -
Nagasawa Jun'ichi,
Yoshida Masaru,
Tamaoki Nobuyuki
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001533
Subject(s) - chemistry , diacetylene , cyclohexane , cyclohexene , hydrogen bond , photopolymer , photochemistry , toluene , intermolecular force , polymer chemistry , organic chemistry , molecule , catalysis , polymer , monomer
Novel macrocyclic diacetylene compounds derived from L ‐glutamic acid and trans ‐1,4‐cyclohexanediol have been synthesized and their gelation ability, photopolymerizability and aggregation state have been studied. Most of the compounds with decyl groups gelatinize hexane, cyclohexane, cyclohexene and carbon tetrachloride. Some of the compounds also gelatinize toluene and 2‐propanol. An FTIR spectroscopy study indicated hydrogen‐bonding in the gel state. An X‐ray crystallographic analysis of one of the macrocyclic compounds with methyl groups demonstrated a tubular assembly based on the face‐to‐face packing of the macrocyclic rings as a result of intermolecular hydrogen‐bonding. Upon photoirradiation, most of the gels changed their hue from colourless to red or orange, which suggests photopolymerization of the diacetylene moieties.