Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism
作者： Jun-Sheng Chen , Pan-Wang Zhou , Song-Qiu Yang , Ai-Ping Fu , Tian-Shu Chu
DOI: 10.1039/C3CP51482J
关键词: Intramolecular force 、 Excited state 、 Fluoride 、 Proton NMR 、 Analytical chemistry 、 Chemistry 、 Physical chemistry 、 Proton 、 Photoinduced electron transfer 、 Density functional theory 、 Ion
摘要: Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of formation fluoride-hydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, theoretical results predicted based on desilylation reaction intramolecular charge (ICT). The reacted with DBM formed an (DBMO), ICT causing red shift in absorbance emission spectra latter. calculated vertical excitation energies ground first excited states both DBMO, as well (1)H NMR spectra, significantly reproduced experimental measurements, providing additional proofs our DBM.
rsc.org
harvard.edu
irgrid.ac.cn参考文章(51)
Christof Hättig, Andreas Köhn, Transition moments and excited-state first-order properties in the coupled-cluster model CC2 using the resolution-of-the-identity approximation Journal of Chemical Physics. ,vol. 117, pp. 6939- 6951 ,(2002) , 10.1063/1.1506918
Yinyin Bao, Bin Liu, Fanfan Du, Jiao Tian, Hu Wang, Ruke Bai, A new strategy for highly selective fluorescent sensing of F− and Zn2+ with dual output modes Journal of Materials Chemistry. ,vol. 22, pp. 5291- 5294 ,(2012) , 10.1039/C2JM16364K
David Balcells, Gregori Ujaque, Inmaculada Fernandez, Noureddine Khiar, Feliu Maseras, Mechanism of the base-assisted displacement of chloride by alcohol in sulfinyl derivatives. Journal of Organic Chemistry. ,vol. 71, pp. 6388- 6396 ,(2006) , 10.1021/JO060546P
Christof Hättig, Florian Weigend, CC2 excitation energy calculations on large molecules using the resolution of the identity approximation Journal of Chemical Physics. ,vol. 113, pp. 5154- 5161 ,(2000) , 10.1063/1.1290013
Jiasheng Wu, Weimin Liu, Jiechao Ge, Hongyan Zhang, Pengfei Wang, New sensing mechanisms for design of fluorescent chemosensors emerging in recent years Chemical Society Reviews. ,vol. 40, pp. 3483- 3495 ,(2011) , 10.1039/C0CS00224K
Sabir H. Mashraqui, Sushil S. Ghorpade, Sapna Tripathi, Smita Britto, A new indole incorporated chemosensor exhibiting selective colorimetric and fluorescence ratiometric signaling of fluoride Tetrahedron Letters. ,vol. 53, pp. 765- 768 ,(2012) , 10.1016/J.TETLET.2011.11.139
Andreas Dreuw, Martin Head-Gordon, Failure of time-dependent density functional theory for long-range charge-transfer excited states: the zincbacteriochlorin-bacteriochlorin and bacteriochlorophyll-spheroidene complexes. Journal of the American Chemical Society. ,vol. 126, pp. 4007- 4016 ,(2004) , 10.1021/JA039556N
Guang-Yue Li, Guang-Jiu Zhao, Yu-Hui Liu, Ke-Li Han, Guo-Zhong He, TD‐DFT study on the sensing mechanism of a fluorescent chemosensor for fluoride: Excited‐state proton transfer Journal of Computational Chemistry. ,vol. 31, pp. 1759- 1765 ,(2010) , 10.1002/JCC.21466
Gustavo E. Scuseria, Curtis L. Janssen, Henry F. Schaefer, An efficient reformulation of the closed‐shell coupled cluster single and double excitation (CCSD) equations The Journal of Chemical Physics. ,vol. 89, pp. 7382- 7387 ,(1988) , 10.1063/1.455269
P. P. Singh, M. k. Barjatiya, S. Dhing, Rekha Bhatnagar, Seema Kothari, Vineet Dhar, Evidence suggesting that high intake of fluoride provokes nephrolithiasis in tribal populations Urological Research. ,vol. 29, pp. 238- 244 ,(2001) , 10.1007/S002400100192