Ethynylated Triphenylamine Monoboronic acid Chemosensors: Experimental and Theoretical Studies

被引：6
作者：
Chi, Lina [1 ]
Wu, Yubo [1 ]
Zhang, Xin [1 ]
Ji, Shaomin [1 ]
Shao, Jingyin [1 ]
Guo, Huimin [2 ]
Wang, Xin [3 ]
Zhao, Jianzhang [1 ]
机构：
[1] Dalian Univ Technol, Sch Chem Engn, State Key Lab Fine Chem, Dalian 116012, Peoples R China
[2] Dalian Univ Technol, Sch Chem Engn, Dept Chem, Dalian 116012, Peoples R China
[3] Sichuan Univ, Fac Chem, Chengdu 610064, Peoples R China
来源：
JOURNAL OF FLUORESCENCE | 2010年 / 20卷 / 06期
关键词：
Boronic acid; Fluorescent chemosensors; DFT; PET; PHOTOINDUCED ELECTRON-TRANSFER; ENANTIOSELECTIVE FLUORESCENT SENSOR; INTRAMOLECULAR CHARGE-TRANSFER; BORONIC ACID; PHOTOPHYSICAL PROPERTIES; ARTIFICIAL RECEPTORS; BISBORONIC ACID; DERIVATIVES; DESIGN; RECOGNITION;
D O I：
10.1007/s10895-010-0677-2
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
New ethynylated triphenylamine boronic acid sensors 1 and 2 were designed and the photophysical properties, as well as the binding with tartaric acid and mandelic acid were studied. We found the emission intensity of the sensors is sensitive to the polarity of the solvents and the emission of sensor 2 is sensitive to protic solvents. Theoretical calculations on the low-lying excited states of these sensors predicted d-PET effect. Experimental observations show either a-PET effect or no significant PET effect for the sensors. The sensitivity of the emission of the sensors toward solvent polarity is used to rationalize the observed emission intensity-pH profiles.
引用
收藏
页码：1255 / 1265
页数：11
相关论文
共 55 条
  • [1] Ophthalmic glucose monitoring using disposable contact lenses - A review
    Badugu, R
    Lakowicz, JR
    Geddes, CD
    [J]. JOURNAL OF FLUORESCENCE, 2004, 14 (05) : 617 - 633
  • [2] Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose
    Cao, HS
    Diaz, DI
    DiCesare, N
    Lakowicz, JR
    Heagy, MD
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1503 - 1505
  • [3] Evaluation of pyranine derivatives in boronic acid based saccharide sensing: Significance of charge interaction between dye and quencher in solution and hydrogel
    Cappuccio, FE
    Suri, JT
    Cordes, DB
    Wessling, RA
    Singaram, B
    [J]. JOURNAL OF FLUORESCENCE, 2004, 14 (05) : 521 - 533
  • [4] Chiral mono boronic acid as fluorescent enantioselective sensor for mono α-hydroxyl carboxylic acids
    Chi, Lina
    Zhao, Jianzhang
    James, Tony D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) : 4684 - 4687
  • [5] Probing Intramolecular B-N Interactions in Ortho-Aminomethyl Arylboronic Acids
    Collins, Byron E.
    Sorey, Steven
    Hargrove, Amanda E.
    Shabbir, Shagufta H.
    Lynch, Vincent M.
    Anslyn, Eric V.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) : 4055 - 4060
  • [6] Solid-state supramolecular structures of resorcinol-arylboronic acid compounds
    Davis, CJ
    Lewis, PT
    Billodeaux, DR
    Fronczek, FR
    Escobedo, JO
    Strongin, RM
    [J]. ORGANIC LETTERS, 2001, 3 (16) : 2443 - 2445
  • [7] Signaling recognition events with fluorescent sensors and switches
    de Silva, AP
    Gunaratne, HQN
    Gunnlaugsson, T
    Huxley, AJM
    McCoy, CP
    Rademacher, JT
    Rice, TE
    [J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1515 - 1566
  • [8] Spectroscopic and photophysical characterization of fluorescent chemosensors for monosaccharides based on N-phenylboronic acid derivatives of 1,8-naphthalimide
    DiCesare, N
    Adhikari, DP
    Heynekamp, JJ
    Heagy, MD
    Lakowicz, JR
    [J]. JOURNAL OF FLUORESCENCE, 2002, 12 (02) : 147 - 154
  • [9] Frisch M. J., 2004, GAUSSIAN 03 REVISION
  • [10] Boronic acids in molecular self-assembly
    Fujita, Norifumi
    Shinkai, Seiji
    James, Tony D.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (07) : 1076 - 1091
123456