Excited State Intramolecular Proton Transfer of Salicylaldehyde Derivatives and Its Application in Fluorescent Probe Field†

doi:10.7503/cjcu20160680

Abstract

Abstract:

According to the electronic structure control theory, the electron withdrawing substituent was introduced to the para-positon of phenol hydroxyl group to stable the ketone conformation, and the target compound, 2-hydroxy-5-(4-cyanophenyl)-benzaldehyde(CN-SA), was prepared. Series of spectral tests show that, CN-SA not only shows the typical excited state intramolecular proton transfer(ESIPT) fluorescence characteristics, but also significantly increases the ketone distribution proportion in radiation transition process, so that the fluorescence intensity and color change visibly. CN-SA not only exhibites selective recognition for the external solvent environment, but also has specific response and quantitative analysis ability for aggregation process(aggregation effect) and the hydrogen bond formation ability following environmental changes(pH effect and anions effect). With little structure tuning, CN-SA could realize alcohol and ketone conformation distribution changes and can be used as a simple multiple stimulation-responsive fluorescence probe.

Key words: Excited state intramolecular proton transfer(ESIPT), Salicylaldehyde, Stimulation-response, Fluorescent probe, Enol-ketone switching

CLC Number:

O644

TrendMD:

LI Xueying, CHEN Yanming, CUI Na, ZHANG Wanyu, WANG Zhiming. Excited State Intramolecular Proton Transfer of Salicylaldehyde Derivatives and Its Application in Fluorescent Probe Field^†[J]. Chem. J. Chinese Universities, 2017, 38(3): 448.

Figures/Tables 8

Fig.1 Structures of SB(A) and SAA(B)

Scheme 1 Transformation from Enol form to ketone form of ESIPT (1) and (3) Enol-form; (2) and (4) ketone-form.

Fig.2 Absorption spectra(A) and emission spectra(B) of CN-SA in different solvent

Fig.3 PL spectra of CN-SA in mixture with different water volume fractions(A) and I/I0-fw versus plot of CN-SA(B) I0 is the PL intensity in pure THF solution. Inset: fluorescence images at fw=0 and 60%.

Fig.4 Absorption spectra(A) and PL spectra(B) of CN-SA in different pH buffers and I/I0-pH plot for CN-SA(C) I0 is the PL intensity at pH=7.0.

Fig.5 Transformation mechanism of CN-SA in different pH buffers

Fig.6 Absorption spectra(A) and PL spectra(B) of CN-SA solution after adding different anions

Fig.7 PL spectra of CN-SA after adding different concentrations of SO42-(λex=340 nm)(A) and PL intensity trend of CN-SA after adding different concentrations of SO42-(B)

References 20

[1]	Li C., Zhang Y., Hu J., Cheng J., Liu S., Angew. Chem. Int. Ed., 2010, 49, 5120—5124
[2]	Chi Z., Zhang X., Xu B., Zhou X., Ma C., Zhang Y., Liu S., Xu J., Chem. Soc. Rev., 2012, 41, 3878—3896
[3]	Stich M. I. J., Fischer L. H., Wolfbeis O. S., Chem. Soc. Rev., 2010, 39, 3102—3114
[4]	Chen F., Zhang J., Wan X., Chem. Eur. J., 2012, 18, 4558—4567
[5]	Levitt J. A., Kuimova M. K., Yahioglu G., Chung P. H., Suhling K., Phillip D., J. Phys. Chem. C, 2009, 113, 11634—11646
[6]	Niu C., Zhao L., Fang T. , Deng X., Ma H., Zhang J., Na N., Han J., Ouyang J., Langmuir,2014, 30, 2351—2359
[7]	Xiang J. F., Yi P. G., Yu X. Y., Chen J., Hao Y. L., Ren Z. Y., Chem. J. Chinese Universities, 2015, 36(4), 654—659
	(向俊峰, 易平贵, 于贤勇, 陈建, 郝艳雷, 任志勇.高等学校化学学报, 2015, 36(4), 654—659)
[8]	Wei R., Song P., Tong A., J. Phys. Chem. C, 2013, 117, 3467—3474
[9]	Peng L., Zhou Z., Wang X., Wei R., Li K., Xiang Y., Tong A., Anal. Chim. Acta, 2014, 829, 54—59
[10]	Wang Z., Gui C., Zhao E., Wang J., Li X., Qin A., Zhao Z., Yu Z., Tang B. Z., ACS Appl. Mater. Interfaces, 2016, 8, 10193—10200
[11]	Smith M.B., March J., March’s Advanced Organic Chemistry, the First Edition, Translated by Li Y. M. , Chemical Industry Press, Beijing, 2009
	(李艳梅[译]艳梅[译]. 高等有机化学反应、机理与结构, 第一版, 北京: 化学工业出版社, 2009)
[12]	Dick B., Ernsting N. P., J. Phys. Chem., 1987, 91, 4261—4265
[13]	Kwon J. E., Park S. Y., Adv. Mater., 2011, 23, 3615—3642
[14]	Mei J, LeungN. L. C., Kwok R. T. K., Lam J. W. Y., Tang B. Z., Chem. Rev., 2015, 115, 11718—11940
[15]	KwokR. T. K., Leung C.W. T., Lam J. W. Y., Tang B. Z., Chem. Soc. Rev., 2015, 44, 4228—4238
[16]	Wang Z., Nie H., Yu Z., Qin A., Zhao Z., Tang B. Z., J. Mater. Chem. C, 2015, 3, 9103—9111
[17]	Liang F. H., Wang D., Ma P. Y, Wang X. H., Chem. Res. Chinese Universities, 2015, 31(5), 724—729
[18]	Kong F., Meng X., Chu R., Xu K., Tang B., Chem. Commun., 2015, 51, 6925—6927
[19]	Yang W. L., Li Q., Wei T. B., Zhang Y. M., Lin Q. Shi B. B., Zhang P., Chem. Res. Chinese Universities, 2013, 29(2), 236—238
[20]	Yeh J. T., Chen W., Liu S., Wu S., New J. Chem., 2014, 38, 4434—4439
	(Ed.:S, Z, M)

Related Articles 15

[1]	ZHAO Yongmei, MU Yeshu, HONG Chen, LUO Wen, TIAN Zhiyong. Bis-naphthalimide Derivatives for Picronitric Acid Detection in Aqueous Solution [J]. Chem. J. Chinese Universities, 2022, 43(3): 20210765.
[2]	TANG Qian, DAN Feijun, GUO Tao, LAN Haichuang. Synthesis and Application of Quinolinone-coumarin-based Colorimetric Fluorescent Probe for Recognition of Hg²⁺ [J]. Chem. J. Chinese Universities, 2022, 43(2): 20210660.
[3]	WANG Di, ZHONG Keli, TANG Lijun, HOU Shuhua, LYU Chunxin. Synthesis of Schiff-based Covalent Organic Framework and Its Recognition of I ^‒ [J]. Chem. J. Chinese Universities, 2022, 43(10): 20220115.
[4]	LI Anran, ZHAO Bing, KAN Wei, SONG Tianshu, KONG Xiangdong, BU Fanqiang, SUN Li, YIN Guangming, WANG Liyan. ON-OFF-ON Double Colorimetric and Fluorescent Probes Based on Phenanthro［9，10-d］imidazole Derivatives and Their Living Cells Imaging [J]. Chem. J. Chinese Universities, 2021, 42(8): 2403.
[5]	HUANG Shan, YAO Jiandong, NING Gan, XIAO Qi, LIU Yi. Efficient Determination of Alkaline Phosphatase Activity Based on Graphene Quantum Dots Fluorescent Probes [J]. Chem. J. Chinese Universities, 2021, 42(8): 2412.
[6]	YANG Xinjie, LAI Yanqiong, LI Qiuyang, ZHANG Yanli, WANG Hongbin, PANG Pengfei, YANG Wenrong. An Enzyme-free and Label-free Fluorescent Probe for Detection of Microcystin-LR Based on Circular DNA-Silver Nanoclusters [J]. Chem. J. Chinese Universities, 2021, 42(12): 3600.
[7]	CHEN Weiju, CHEN Shiya, XUE Caoye, LIU Bo, ZHENG Jing. Fluorescent Probe for Hypoxia-triggered Imaging and Cancer Therapy [J]. Chem. J. Chinese Universities, 2021, 42(11): 3433.
[8]	HUANG Jialing,LIU Fengjiao,WANG Tingting,LIU Cuie,ZHENG Fengying,WANG Zhenhong,LI Shunxing. Nitrogen and Sulfur co-Doped Carbon Quantum Dots for Accurate Detection of pH in Gastric Juice^† [J]. Chem. J. Chinese Universities, 2020, 41(7): 1513.
[9]	WU Qian, CHENG Dan, LÜ Yun, YUAN Lin, ZHANG Xiaobing. Monitoring of Peroxynitrite Variation During Liver Injury Adopting a Far Red to Near-infrared Fluorescent Probe with Large Stokes Shift [J]. Chem. J. Chinese Universities, 2020, 41(11): 2426.
[10]	ZHANG Danfeng, ZHAO Maoyu, GUO Ning, TANG Songchao, ZHENG Anna. “One-pot”N-(2-Benzamidophenyl)-salicylaldehyde Imine/TiCl₄·2THF for Catalytic Ethylene Polymerization ^† [J]. Chem. J. Chinese Universities, 2019, 40(9): 2012.
[11]	WANG Jinjin,QI Shaolong,DU Jianshi,YANG Qingbiao,SONG Yan,LI Yaoxian. Synthesis of Benzothiazole Fluorescent Probe for Detection of N₂H₄·H₂O and HS $O 3 - †$ [J]. Chem. J. Chinese Universities, 2019, 40(7): 1397.
[12]	Yong ZHANG,Cheng SHEN,Zhirong XING,Guiqi CHEN,Zi LU,Zhibing HOU,Xuemei CHEN. Benzimidazole-Derived Fluorescence Enhancement Probe for Visual Detection of HClO ^† [J]. Chem. J. Chinese Universities, 2019, 40(12): 2480.
[13]	YANG Mei,LIU Qing,TANG Qing,WANG Chenghui,YANG Meixiang,SUN Tao,HUANG Ying,TAO Zhu. Water-soluble Supramolecular Fluorescent Probe for Sensing Carbendazim and Its Application in Living Cell Imaging^† [J]. Chem. J. Chinese Universities, 2018, 39(12): 2665.
[14]	HE Xiaoqin, HE Junlin, XU Hua, GUO Lei, XIE Jianwei. Active Conformation of DNA Aptamer Against Recombinant Human Erythropoietin-α^† [J]. Chem. J. Chinese Universities, 2018, 39(1): 48.
[15]	LIU Huiqiang, PENG Chao, CHEN Ning, LIU Yangping. Novel Fluorescent/EPR Difunctional Probe for Detecting Hypochlorite^† [J]. Chem. J. Chinese Universities, 2017, 38(9): 1542.