Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2-Anthracenecarboxylic Acid
Regioselective Molecularly Imprinted Reaction Field for [4 + 4] Photocyclodimerization of 2-Anthracenecarboxylic Acid
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2-蒽甲酸[4 4]光环二聚反应的区域选择性分子印迹反应场
DOI：
10.1021/acs.langmuir.6b04104
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发表时间：
2017
期刊：
影响因子：
3.9
通讯作者：
Nakai Satoshi; Sunayama Hirobumi; Kitayama Yukiya; Takeuchi Toshifumi; Nishijima Masaki; Inoue Yoshihisa; Wada Takehiko
中科院分区：
文献类型：
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作者：
鈴木泰成;藤井啓祐;小芦雅斗;Nakai Satoshi; Sunayama Hirobumi; Kitayama Yukiya; Takeuchi Toshifumi; Nishijima Masaki; Inoue Yoshihisa; Wada Takehiko
分子印迹空腔可作为2-蒽甲酸（2-AC）[4 + 4]光环二聚反应的区域选择性反应场。以N-甲基丙烯酰基-4-氨基苯甲脒为功能单体，与模板2-AC和乙二醇二甲基丙烯酸酯为交联单体，通过沉淀聚合形成复合物，制备了分子印迹聚合物。2-AC-印迹腔，从而构建优先结合2-AC的亲和力大于对结构相关的9-蒽羧酸，2-氨基蒽，和未取代的蒽。此外，从四种可能的区域异构体环二聚体中，它们特异性地介导2-AC的[4 + 4]光环二聚化为抗-头-尾（anti-HT）异构体。这表明印迹空腔以抗HT的方式容纳两个2-AC分子，从而促进随后的区域选择性光环化二聚。
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 ofN-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 theanti-head-to-tail (anti-HT) isomer. This indicates that the imprinted cavities accommodate two 2-AC molecules in ananti-HT manner, thereby facilitating the subsequent regioselective photocyclodimerization.