RETRACTED: A Core-Substituted Naphthalene Diimide Fluoride Sensor (Retracted Article)

被引:192
作者
Bhosale, Sheshanath V. [1 ]
Bhosale, Sidhanath V. [2 ]
Kalyankar, Mohan B. [1 ,2 ]
Langford, Steven J. [1 ]
机构
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
[2] N Maharashtra Univ, Dept Organ Chem, Jalgaon 425001, India
基金
澳大利亚研究理事会;
关键词
COLORIMETRIC ANION SENSORS; THIOUREA BINDING-SITES; OLIGOINDOLE FOLDAMERS; PROTON-TRANSFER; LIPID-BILAYERS; RECEPTORS; UREA; RECOGNITION; HYDROGEN; WATER;
D O I
10.1021/ol9022722
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and characterization of a highly fluorescent core-substituted naphthalene diimide sensor (phi = 0.34) bearing a bis-sulfonamide group is described. The compound shows a unique selectivity and reactivity for the fluoride ion over other anions in CHCl3 by a two-stage deprotonation process leading to a colorimetric response. In DMSO solution, the sensor is shown to be highly selective for fluoride (K-a similar to 10(6) M-1) over other anions with more pronounced changes In absorption characteristics.
引用
收藏
页码:5418 / 5421
页数:4
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共 62 条
  • [1] Transition metal and organometallic anion complexation agents
    Beer, PD
    Hayes, EJ
    [J]. COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) : 167 - 189
  • [2] Abiotic guanidinium containing receptors for anionic species
    Best, MD
    Tobey, SL
    Anslyn, EV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) : 3 - 15
  • [3] Synthetic functional π-stack architecture in lipid bilayers
    Bhosale, Sheshanath
    Sisson, Adam L.
    Sakai, Naomi
    Matile, Stefan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (16) : 3031 - 3039
  • [4] Photoproduction of proton gradients with π-stacked fluorophore scaffolds in lipid bilayers
    Bhosale, Sheshanath
    Sisson, Adam L.
    Talukdar, Pinaki
    Fuerstenberg, Alexandre
    Banerji, Natalie
    Vauthey, Eric
    Bollot, Guillaume
    Mareda, Jiri
    Roger, Cornelia
    Wuerthner, Frank
    Sakai, Naomi
    Matile, Stefan
    [J]. SCIENCE, 2006, 313 (5783) : 84 - 86
  • [5] Chemistry of naphthalene diimides
    Bhosale, Sheshanath V.
    Jani, Chintan H.
    Langford, Steven J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) : 331 - 342
  • [6] Dipyrrolylquinoxalines: Efficient sensors for fluoride anion in organic solution
    Black, CB
    Andrioletti, B
    Try, AC
    Ruiperez, C
    Sessler, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) : 10438 - 10439
  • [7] Nature of urea-fluoride interaction:: Incipient and definitive proton transfer
    Boiocchi, M
    Del Boca, L
    Gómez, DE
    Fabbrizzi, L
    Licchelli, M
    Monzani, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) : 16507 - 16514
  • [8] Anion receptor chemistry: highlights from 2007
    Caltagirone, Claudia
    Gale, Philip A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) : 520 - 563
  • [9] 1,3-Diindolylureas: high affinity dihydrogen phosphate receptors
    Caltagirone, Claudia
    Gale, Philip A.
    Hiscock, Jennifer R.
    Brooks, Simon J.
    Hursthouse, Michael B.
    Light, Mark E.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (26) : 3007 - 3009
  • [10] Anion binding vs. sulfonamide deprotonation in functionalised ureas
    Caltagirone, Claudia
    Bates, Gareth W.
    Gale, Philip A.
    Light, Mark E.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (01) : 61 - 63