Why, on interaction of urea-based receptors with fluoride, beautiful colors develop

被引:488
作者
Esteban-Gómez, D [1 ]
Fabbrizzi, L [1 ]
Licchelli, M [1 ]
机构
[1] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy
关键词
D O I
10.1021/jo050528s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Urea-based receptors, containing electron-withdrawing chromogenic substituents, in a DMSO solution, in the presence of varying excess of fluoride, do not form H-bond complexes, but undergo stepwise deprotonation of the two N-H fragments, an event which is signaled by the development of vivid colors. Double deprotonation is also observed in the presence of hydroxide. Less basic anions (CH3COO-, H2PO4-) induce deprotonation of only one N-H.
引用
收藏
页码:5717 / 5720
页数:4
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共 26 条
[1]   Nature of urea-fluoride interaction:: Incipient and definitive proton transfer [J].
Boiocchi, M ;
Del Boca, L ;
Gómez, DE ;
Fabbrizzi, L ;
Licchelli, M ;
Monzani, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16507-16514
[2]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[3]   MOLECULAR RECOGNITION - HYDROGEN-BONDING RECEPTORS THAT FUNCTION IN HIGHLY COMPETITIVE SOLVENTS [J].
FAN, E ;
VANARMAN, SA ;
KINCAID, S ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :369-370
[4]   Special issue: 35 years of synthetic anion receptor chemistry 1968-2003 - Preface [J].
Gale, PA .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :1-1
[5]   Synthesis and luminescence properties of novel ferrocene-naphthalimides dyads [J].
Gan, J ;
Tian, H ;
Wang, ZH ;
Chen, KH ;
Hill, J ;
Lane, PA ;
Rahn, MD ;
Fox, AM ;
Bradley, DDC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :168-175
[6]   Fluoride ion receptors based on dipyrrolyl derivatives bearing electron-withdrawing groups: Synthesis, optical and electrochemical sensing, and computational studies [J].
Ghosh, T ;
Maiya, BG ;
Wong, MW .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51) :11249-11259
[7]   THEORETICAL-STUDIES OF PROTON TRANSFERS .1. THE POTENTIAL-ENERGY SURFACES OF THE IDENTITY REACTIONS OF THE 1ST-ROW AND 2ND-ROW NONMETAL HYDRIDES WITH THEIR CONJUGATE BASES [J].
GRONERT, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10258-10266
[8]   Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites [J].
Jose, DA ;
Kumar, DK ;
Ganguly, B ;
Das, A .
ORGANIC LETTERS, 2004, 6 (20) :3445-3448
[9]   Synthesis and anion recognition properties of 8,8′-dithioureido-2,2′-binaphthalene [J].
Kondo, S ;
Nagamine, M ;
Yano, Y .
TETRAHEDRON LETTERS, 2003, 44 (49) :8801-8804
[10]   A colorimetric and ratiometric fluorescent chemosensor with three emission changes: Fluoride ion sensing by a triarylborane-porphyrin conjugate [J].
Kubo, Y ;
Yamamoto, M ;
Ikeda, M ;
Takeuchi, M ;
Shinkai, S ;
Yamaguchi, S ;
Tamao, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2036-2040