Liao Jen-Hai, Chen Chao-Tsen, Chou He-Chun, Cheng Chung-Chih, Chou Pi-Tai, Fang Jim-Min, Slanina Zdenek, Chow Tashin J
Department of Chemistry, National Taiwan University, Taipei, 106, Republic of China.
Org Lett. 2002 Sep 5;4(18):3107-10. doi: 10.1021/ol0264096.
[structure: see text] A push-pull conjugated molecule, 2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN), has been designed to bind selectively with octyl glucopyranoside (OGU). The BPN/OGU quadruple hydrogen-bonding complex adopts a rigid BPN conformation in which the proton donor (d) and acceptor (a) relays (daad) are resonantly conjugated through the ethynyl bridge, inducing pi-electron delocalization, i.e., a charge transfer effect. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of approximately 100 pM.
[结构：见正文] 一种推挽共轭分子，2,7-双(1H-吡咯-2-基)乙炔基-1,8-萘啶（BPN），已被设计用于与辛基吡喃葡萄糖苷（OGU）选择性结合。BPN/OGU四重氢键复合物采用刚性的BPN构象，其中质子供体（d）和受体（a）中继（daad）通过乙炔基桥共振共轭，诱导π电子离域，即电荷转移效应。优异的光物理性质使BPN成为监测吡喃葡萄糖苷的高灵敏度探针，检测限约为100 pM。
