title: A phenylbenzothiazole derived fluorescent sensor for Zn(II) recognition in aqueous solution through "turn-on" excited-state intramolecular proton transfer emission.
abstract: A highly selective and sensitive fluorescent Zn(2+) sensor N-(2-(benzo[d]thiazol-2-yl)phenyl)-2-((pyridin-2-ylmethyl)amino)acetamide (1) that derived from 2-(2'-aminophenyl)benzothiazole has been developed. In aqueous solution (HEPES/CH3CN=4/6, v/v, HEPES 20 mM, pH = 7.4), sensor 1 displays highly selective recognition to Zn(2+) over other metal ions with a distinct longer-wavelength emission enhancement. Sensor 1 binds Zn(2+) through its amide form with a 1:1 binding stoichiometry, which switched on the excited-state intramolecular proton transfer (ESIPT).
authors.affiliation: Department of Chemistry, Liaoning Provincial Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University, Jinzhou, 121013, China, ljtang@bhu.edu.cn.
authors.forename: Lijun
authors.initials: L
authors.lastname: Tang
authors.forename: Xin
authors.initials: X
authors.lastname: Dai
authors.forename: Keli
authors.initials: K
authors.lastname: Zhong
authors.forename: Xin
authors.initials: X
authors.lastname: Wen
authors.forename: Di
authors.initials: D
authors.lastname: Wu
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011522:Protons; D012996:Solutions; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D015032:Zinc / Q000032:analysis*
chemical_list: D005456:Fluorescent Dyes; D011522:Protons; D012996:Solutions; D013844:Thiazoles; D014867:Water; C070845:2-phenylbenzothiazole; D015032:Zinc
references.citation: Dalton Trans. 2011 Feb 21;40(7):1503-9
references.pmid: 21243147
references.citation: J Am Chem Soc. 2004 Jan 28;126(3):712-3
references.pmid: 14733534
references.citation: Chem Commun (Camb). 2009 Apr 7;(13):1736-8
references.pmid: 19294279
references.citation: Chem Mater. 2010 Jun 8;22(11):3472-3481
references.pmid: 20577581
references.citation: J Org Chem. 2012 Apr 6;77(7):3670-3
references.pmid: 22420536
references.citation: Org Biomol Chem. 2012 Nov 28;10(44):8753-7
references.pmid: 23032481
references.citation: J Am Chem Soc. 2006 May 24;128(20):6548-9
references.pmid: 16704241
references.citation: Chem Commun (Camb). 2013 Apr 28;49(33):3434-6
references.pmid: 23507903
references.citation: Anal Chim Acta. 2011 Feb 14;687(1):82-8
references.pmid: 21241850
references.citation: Chem Soc Rev. 2010 Jun;39(6):1996-2006
references.pmid: 20428518
references.citation: Anal Chem. 2010 Apr 15;82(8):3108-13
references.pmid: 20334436
references.citation: Nature. 1991 Feb 7;349(6309):521-4
references.pmid: 1846946
references.citation: Biomaterials. 2012 Nov;33(31):7818-27
references.pmid: 22871424
references.citation: Chem Commun (Camb). 2013 Aug 21;49(65):7228-30
references.pmid: 23838617
references.citation: J Org Chem. 2001 Nov 2;66(22):7328-33
references.pmid: 11681945
references.citation: J Am Chem Soc. 2010 Jan 20;132(2):601-10
references.pmid: 20000765
references.citation: Inorg Chem. 2009 Aug 17;48(16):7630-8
references.pmid: 19591460
references.citation: Chem Commun (Camb). 2012 May 16;48(39):4764-6
references.pmid: 22472965
references.citation: Chemistry. 2004 Jun 21;10(12):3015-25
references.pmid: 15214085
references.citation: J Phys Chem A. 2013 Apr 25;117(16):3387-95
references.pmid: 23530703
references.citation: Chem Soc Rev. 2007 Jun;36(6):993-1017
references.pmid: 17534482
references.citation: Chemistry. 2009;15(20):5096-103
references.pmid: 19343759
references.citation: Chemistry. 2007;13(13):3630-5
references.pmid: 17238212
references.citation: Science. 1996 May 17;272(5264):1013-6
references.pmid: 8638123
references.citation: Chem Asian J. 2013 Jul;8(7):1441-6
references.pmid: 23640780
references.citation: J Am Chem Soc. 2009 Feb 11;131(5):2008-12
references.pmid: 19191706
references.citation: J Am Chem Soc. 2007 Nov 7;129(44):13447-54
references.pmid: 17927174
references.citation: Science. 2001 Jun 29;292(5526):2488-92
references.pmid: 11397910
references.citation: Org Biomol Chem. 2011 Apr 7;9(7):2345-9
references.pmid: 21311797
references.citation: Neurobiol Dis. 1997;4(3-4):137-69
references.pmid: 9361293
references.citation: Anal Chem. 1996 Apr 15;68(8):1414-8
references.pmid: 8651501
references.citation: J Biol Chem. 1994 Apr 22;269(16):12152-8
references.pmid: 8163520
references.citation: Acc Chem Res. 2009 Jan 20;42(1):193-203
references.pmid: 18989940
references.citation: J Org Chem. 2008 Nov 7;73(21):8212-8
references.pmid: 18817447
references.citation: Org Biomol Chem. 2011 Dec 21;9(24):8284-7
references.pmid: 22051892