Visible Light Excitable SCN^- Selective Fluorescence Probe Derived from Thiophene

An efficient fluorescence probe, 4-methyl-2,6-bis（（thiophen-2-ylmethylimino）methyl）phenol （DFPTMA） and its SCN adduct has been synthesized and characterized by different spectroscopic techniques like ^1H NMR,^13C NMR, QTOF-MS ES^＋, UV-Vis and FTIR spectroscopy. Single crystal X-ray structure of DFPT...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 33; no. 10; pp. 1173 - 1177
Main Authors Das, Sudipta, Lohar, Sisir, Matalobos, Jesús Sanmartín, Das, Debasis
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.10.2015
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Multidisciplinary
fluorescence
Physical Sciences
Science & Technology
SCN
Spectrum analysis
thiophene derivative
visible light excitation
X射线结构
光激发
光谱技术
噻吩
紫外可见光谱
红外光谱
荧光探针
COMPLEXES
AL3
LEVEL DETERMINATION
HETEROACENE
AQUEOUS-SOLUTION
visible light excitation
CHEMOSENSOR
TRANSPORT
fluorescence
THIOCYANATE LEVELS
thiophene derivative
ANION RECOGNITION
CYSTIC-FIBROSIS
SCN
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Summary:An efficient fluorescence probe, 4-methyl-2,6-bis（（thiophen-2-ylmethylimino）methyl）phenol （DFPTMA） and its SCN adduct has been synthesized and characterized by different spectroscopic techniques like ^1H NMR,^13C NMR, QTOF-MS ES^＋, UV-Vis and FTIR spectroscopy. Single crystal X-ray structure of DFPTMA is reported. In presence of SCN-, DFPTMA exhibits significant fluorescence enhancement （λEx, 455 nm, λEm, 504 nm） in aqueous methanol （water-methanol, 1 ： 4, V/V, 0.1 mol/L HEPES buffer, pH 7.4）. Common bio-relevant anions viz. CH3COO^-, NO2, NO7, Cl^-, Br^-, I^-, SO4^2-, HSO4^-, N3^-, HAsO4^2-, Cr2O7^2-, H2PO4, ClO4^-, NCO^-, CN^-, CO3^2-, F^-, PO4^3-, S2-, HS- do not interfere in the recognition of SCN-. Lowest detection limit for SCN^- is 0.88 μmol/L with response time 〈5 min. The SCN assisted enhancement in emission intensity may be attributed to the formation of H-bond which enhances the rigidity of the molecular assembly.
Bibliography:An efficient fluorescence probe, 4-methyl-2,6-bis（（thiophen-2-ylmethylimino）methyl）phenol （DFPTMA） and its SCN adduct has been synthesized and characterized by different spectroscopic techniques like ^1H NMR,^13C NMR, QTOF-MS ES^＋, UV-Vis and FTIR spectroscopy. Single crystal X-ray structure of DFPTMA is reported. In presence of SCN-, DFPTMA exhibits significant fluorescence enhancement （λEx, 455 nm, λEm, 504 nm） in aqueous methanol （water-methanol, 1 ： 4, V/V, 0.1 mol/L HEPES buffer, pH 7.4）. Common bio-relevant anions viz. CH3COO^-, NO2, NO7, Cl^-, Br^-, I^-, SO4^2-, HSO4^-, N3^-, HAsO4^2-, Cr2O7^2-, H2PO4, ClO4^-, NCO^-, CN^-, CO3^2-, F^-, PO4^3-, S2-, HS- do not interfere in the recognition of SCN-. Lowest detection limit for SCN^- is 0.88 μmol/L with response time 〈5 min. The SCN assisted enhancement in emission intensity may be attributed to the formation of H-bond which enhances the rigidity of the molecular assembly.
31-1547/O6
visible light excitation, SCN^-, fluorescence, thiophene derivative
istex:6CAA01CCD8F2530386A46FE2822EFE6B2D52E710
ArticleID:CJOC201500499
ark:/67375/WNG-2F65DNLX-4
West Bengal Council of Science and Technology (DST, Govt. of W. B.)
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201500499