TY - JOUR
T1 - Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2-Anthracenecarboxylic Acid
AU - Nakai, Satoshi
AU - Sunayama, Hirobumi
AU - Kitayama, Yukiya
AU - Nishijima, Masaki
AU - Wada, Takehiko
AU - Inoue, Yoshihisa
AU - Takeuchi, Toshifumi
N1 - Publisher Copyright:
© 2017 American Chemical Society.
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2017/3/7
Y1 - 2017/3/7
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.langmuir.6b04104
DO - 10.1021/acs.langmuir.6b04104
M3 - Article
C2 - 28177241
AN - SCOPUS:85014789000
VL - 33
SP - 2103
EP - 2108
JO - Langmuir
JF - Langmuir
SN - 0743-7463
IS - 9
ER -