Kim Sook-Hee, Hong Seong-Jin, Yoo Jaeduk, Kim Sung Kuk, Sessler Janathan L, Lee Chang-Hee
Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University, Chun-Chon 200-701, Korea.
Org Lett. 2009 Aug 20;11(16):3626-9. doi: 10.1021/ol901361h.
A strapped calix[4]pyrrole bearing a 1,3-indanedione group at a beta-pyrrolic position has been synthesized and studied as a ratiometric cyanide-selective chemosensor. A concentration-dependent bleaching of the initial yellow color was observed upon addition of the cyanide anion. The bleaching, which was observed exclusively with the cyanide anion, occurred even in the presence of other anions. Spectroscopic studies provide support for a mechanistic interpretation wherein the cyanide anion forms a complex with the receptor (K = 2.78 x 10(4) M(-1)) through a fast equilibrium, which is followed by slow nucleophilic addition to the beta-position of the 1,3-indanedione group. A minimum inhibitory effect from other anions was observed, a feature that could be beneficial in the selective sensing of the cyanide anion.
已合成了一种在β-吡咯位置带有1,3-茚二酮基团的束缚杯[4]吡咯，并将其作为比例型氰化物选择性化学传感器进行了研究。加入氰化物阴离子后，观察到初始黄色出现浓度依赖性褪色。这种褪色仅在氰化物阴离子存在时观察到，即使在其他阴离子存在的情况下也会发生。光谱研究为一种机理解释提供了支持，即氰化物阴离子通过快速平衡与受体形成络合物（K = 2.78 x 10(4) M(-1)），随后缓慢亲核加成到1,3-茚二酮基团的β位。观察到其他阴离子的最小抑制作用，这一特性可能有利于氰化物阴离子的选择性传感。
