Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

被引：186
作者：
Goswami, Shymaprosad [1 ]
Manna, Abhishek [1 ]
Paul, Sima [1 ]
Das, Avijit K. [1 ]
Aich, Krishnendu [1 ]
Nandi, Prasanta K. [1 ]
机构：
[1] Bengal Engn & Sci Univ, Sibpur 711103, Howrah, India
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 28期
关键词：
INTRAMOLECULAR PROTON-TRANSFER; LUMINESCENCE; MOTION; ION;
D O I：
10.1039/c3cc39256b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
For ratiometric "naked eye'' detection of CN-, an ESIPT exhibiting benzothiazole receptor (BHI) is designed having one aldehyde group ortho and the other aldehyde para to the OH group respectively. Due to RAHBs, the ortho aldehyde group is highly reactive undergoing nucleophilic cyanide addition selectively, which hampered ESIPT. This is also supported by DFT and TD-DFT calculations.
引用
收藏
页码：2912 / 2914
页数：3
相关论文
共 27 条
  • [1] [Anonymous], 1999, ULLMANS ENCY IND CHE
  • [2] Baird C.i Cann., 2005, Environmental chemistry
  • [3] A "naked eye'' and ratiometric fluorescent chemosensor for rapid detection of F- based on combination of desilylation reaction and excited-state proton transfer
    Bao, Yinyin
    Liu, Bin
    Wang, Hu
    Tian, Jiao
    Bai, Ruke
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 3957 - 3959
  • [4] A Highly Selective Pyrophosphate Sensor Based on ESIPT Turn-On in Water
    Chen, Wei-Hua
    Xing, Yu
    Pang, Yi
    [J]. ORGANIC LETTERS, 2011, 13 (06) : 1362 - 1365
  • [5] Vibrational coherence in ultrafast excited state proton transfer
    Chudoba, C
    Riedle, E
    Pfeiffer, M
    Elsaesser, T
    [J]. CHEMICAL PHYSICS LETTERS, 1996, 263 (05) : 622 - 628
  • [6] Proton-transfer reaction dynamics
    Douhal, A
    Lahmani, F
    Zewail, AH
    [J]. CHEMICAL PHYSICS, 1996, 207 (2-3) : 477 - 498
  • [7] A reaction-based chromogenic and fluorescent chemodosimeter for fluoride anions
    Fu, Li
    Jiang, Feng-Lei
    Fortin, Daniel
    Harvey, Pierre D.
    Liu, Yi
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (19) : 5503 - 5505
  • [8] EVIDENCE FOR RESONANCE-ASSISTED HYDROGEN-BONDING FROM CRYSTAL-STRUCTURE CORRELATIONS ON THE ENOL FORM OF THE BETA-DIKETONE FRAGMENT
    GILLI, G
    BELLUCCI, F
    FERRETTI, V
    BERTOLASI, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) : 1023 - 1028
  • [9] Gilli G., 2009, NATURE HYDROGEN BOND
  • [10] Goswami S., 2013, TETRAHEDRON LETT
123