Two-Photon Sensors for Proton Derived from 7-Pyridinylbenzo[c] [1,2,5]thiadiazole Receptor
ZHAO Wei-feng1, WANG Xiao-mei2*, LUO Jian-fang2, TAO Xu-tang3
1. Institute of Chemistry and Materials Science, Soochow University, Suzhou 215123, China 2. Institute of Chemistry and Bioengineering, Suzhou University of Science and Technology, Suzhou 215009, China3, State Key Laboratory of Crystal Materials, Shandong University, Ji’nan 250100, China
Abstract:Two new chromophores with carbazole as molecular focal point bearing either one o-pyridine-benzothiadiazole unit or two o-pyridine-benzothiadiazole units at the periphery respectively, named as 2,8-(o-pyridine-benzothiadiazole)-N-ethyl-carbazole (CPTZ1) and 2,8-bis(o-pyridine-benzothiadiazole)-N-ethyl-carbazole (CPTZ2), were synthesized and characterized by IR spectra, 1H NMR spectra and MS. The influence of proton upon one-photon and two-photon fluorescence about these two compounds was discussed. Stern-Volmer equation gives that the S-V constants (k1PSV) of one-photon fluorescence (1PF) of CPTZ1 and CPTZ2 are 0.04 and 0.10 L·mol-1, respectively; while the k2PSV of two-photon fluorescence (2PF) of CPTZ1 and CPTZ2 are 0.20 and 0.22 L·mol-1, respectively. Obviously, two-photon (2P) fluorescence detection presented more sensitivity than one-photon (1P) fluorescence response, which exhibits the potential application of two-photon sensor in PH detection.
[1] Saari L A, Seitz W R. Anal. Chem., 1982, 54: 821. [2] Lobnik A, Oehme I, Murkovic I,et al. Anal. Chim. Acta,1998, 367: 159. [3] Liu Y H, Dam T H, Panuano P A. Anal. Chim. Acta, 2000, 419: 215. [4] Ma L Y, Wang H Y, Xie H,et al. Spectrochim. Acta Part A, 2004, 60: 1865. [5] Liebsch G, Klimant I, Krause C,et al. Anal. Chem., 2001, 73: 4354. [6] Liebsch G, Klimant I, Krause C,et al. Anal. Chem., 1998, 70: 3892. [7] Li Z Z, Niu C G, Zeng G M,et al. Sens. Actuators B, 2006, 114: 308. [8] Niu C G, Gui X Q, Zeng G M,et al. Analyst, 2005, 130(11): 1551. [9] Prissanaroon-Ouajai W,Pigram P J,Jones R,et al. Sens. Actuators B Chem.,2009, 138:504. [10] Niu C G, Gui X Q, Zeng G M, et al. Anal. Bioanal. Chem., 2005, 383(2): 349. [11] Wang X M,Zhou Y F,Yu W T. J. Mater. Chem., 2000, 10:2698. [12] Wang X M, Wang D, Zhou G Y. J. Mater. Chem., 2001, 11:1600. [13] Pu S Z, Fan C B, Miao W J,et al. Dyes and Pigments, 2010, 84:25. [14] LIU Guo-hua, YANG Ping, JIANG Wan-li,et al(刘国华,杨 平,蒋宛莉,等). Journal of Functional Materials(功能材料),2005, 5(36): 600.