Engineering 1,3-Alternate Calixcarbazole for Recognition and Sensing of Bisphenol F in Water.
Herein, we report a carbazolyl tubular macrocycle (3), which possesses a "π-tube" capable of encapsulating and sensing bisphenol F (BPF), which is a toxic industrial material. In this work, the synthesis of 3, its conformation in solution as well as its binding property to BPF have been investigated. Nuclear magnetic resonance (NMR), ultraviolet-visible light (UV-vis), fluorescence spectra, and molecular modeling studies reveal that the "π-tube" of 3 in 1,3-alternate conformation could encapsulate BPF with 1:1 binding stoichiometry in water, with its orthogonal tweezers sandwiching the two phenol units of BPF. Moreover, 3 could serve as a sensitive fluorescent probe for BPF (limitation of detection = 157 nM).
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Gang
G
Li
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Liang
L
Zhao
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Peng
P
Yang
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Zhaozheng
Z
Yang
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Zhangmin
Z
Tian
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Yan
Y
Chen
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Hongyan
H
Shen
Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University) , Ministry of Education, Shenyang 110016, People's Republic of China.
Chun
C
Hu