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Reference type: Journal
Authors: Nakai S, Sunayama H, Kitayama Y, Nishijima M, Wada T, Inoue Y, Takeuchi T
Article Title: Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2-Anthracenecarboxylic Acid.
Publication date: 2017
Journal: Langmuir
Volume: 33
Issue: (9)
Page numbers: 2103-2108.
DOI: 10.1021/acs.langmuir.6b04104

Abstract: Molecularly imprinted cavities have functioned as a regioselective reaction field for the [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (2-AC). Molecularly imprinted polymers were prepared by precipitation polymerization of N-methacryloyl-4-aminobenzamidine as a functional monomer to form a complex with template 2-AC and ethylene glycol dimethacrylate as a crosslinking monomer. The 2-AC-imprinted cavities thus constructed preferentially bound 2-AC with an affinity greater than that toward structurally related 9-anthracenecarboxylic acid, 2-aminoanthracene, and unsubstituted anthracene. Moreover, from the four possible regioisomeric cyclodimers, they mediated the [4 + 4] photocyclodimerization of 2-AC specifically to the anti-head-to-tail (anti-HT) isomer. This indicates that the imprinted cavities accommodate two 2-AC molecules in an anti-HT manner, thereby facilitating the subsequent regioselective photocyclodimerization
Template and target information: 2-anthracenecarboxylic acid, 2-AC

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