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Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2‑Anthracenecarboxylic Acid

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journal contribution
posted on 08.02.2017, 00:00 by Satoshi Nakai, Hirobumi Sunayama, Yukiya Kitayama, Masaki Nishijima, Takehiko Wada, Yoshihisa Inoue, Toshifumi Takeuchi
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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