A Triphenyl Amine-Based Solvatofluorochromic Dye for the Selective and Ratiometric Sensing of OCl− in Human Blood Cells
A new visible‐light‐excitable fluorescence ratiometric probe for OCl− has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single‐crystal X‐ray analysis. It behaves as a highly selective and sensitive probe for OCl− over other analyt...
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| Published in | Chemistry, an Asian journal Vol. 10; no. 3; pp. 694 - 700 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.03.2015
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | A new visible‐light‐excitable fluorescence ratiometric probe for OCl− has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single‐crystal X‐ray analysis. It behaves as a highly selective and sensitive probe for OCl− over other analytes with a fast response time (∼100 s). OCl− reacts with the probe leading to the formation of the corresponding aldehyde in a mixed‐aqueous system. The detection limit of the probe is in the 10−8 M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non‐polar to polar, the emission band of TAM largely red‐shifted. Moreover, the probe shows an excellent performance in real‐life application in detecting OCl− in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl− were studied by DFT and TDDFT computational calculations.
Green means danger! A new triphenyl amine‐diaminomaleonitrile‐based probe was synthesized. This probe acts as a polarity probe with a strong positive emission solvatofluorochromism. It exclusively detects OCl− in a ratiometric manner in a mixed aqueous system with a detection limit of about 10−8 M. Moreover, it can detect OCl− in vivo in human blood cells. |
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| AbstractList | A new visible-light-excitable fluorescence ratiometric probe for OCl(-) has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single-crystal X-ray analysis. It behaves as a highly selective and sensitive probe for OCl(-) over other analytes with a fast response time (∼100 s). OCl(-) reacts with the probe leading to the formation of the corresponding aldehyde in a mixed-aqueous system. The detection limit of the probe is in the 10(-8) M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non-polar to polar, the emission band of TAM largely red-shifted. Moreover, the probe shows an excellent performance in real-life application in detecting OCl(-) in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl(-) were studied by DFT and TDDFT computational calculations. A new visible-light-excitable fluorescence ratiometric probe for OCl(-) has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single-crystal X-ray analysis. It behaves as a highly selective and sensitive probe for OCl(-) over other analytes with a fast response time (∼100 s). OCl(-) reacts with the probe leading to the formation of the corresponding aldehyde in a mixed-aqueous system. The detection limit of the probe is in the 10(-8) M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non-polar to polar, the emission band of TAM largely red-shifted. Moreover, the probe shows an excellent performance in real-life application in detecting OCl(-) in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl(-) were studied by DFT and TDDFT computational calculations.A new visible-light-excitable fluorescence ratiometric probe for OCl(-) has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single-crystal X-ray analysis. It behaves as a highly selective and sensitive probe for OCl(-) over other analytes with a fast response time (∼100 s). OCl(-) reacts with the probe leading to the formation of the corresponding aldehyde in a mixed-aqueous system. The detection limit of the probe is in the 10(-8) M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non-polar to polar, the emission band of TAM largely red-shifted. Moreover, the probe shows an excellent performance in real-life application in detecting OCl(-) in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl(-) were studied by DFT and TDDFT computational calculations. A new visible‐light‐excitable fluorescence ratiometric probe for OCl − has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single‐crystal X‐ray analysis. It behaves as a highly selective and sensitive probe for OCl − over other analytes with a fast response time (∼100 s). OCl − reacts with the probe leading to the formation of the corresponding aldehyde in a mixed‐aqueous system. The detection limit of the probe is in the 10 −8 M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non‐polar to polar, the emission band of TAM largely red‐shifted. Moreover, the probe shows an excellent performance in real‐life application in detecting OCl − in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl − were studied by DFT and TDDFT computational calculations. A new visible-light-excitable fluorescence ratiometric probe for OCl- has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single-crystal X-ray analysis. It behaves as a highly selective and sensitive probe for OCl- over other analytes with a fast response time (100s). OCl- reacts with the probe leading to the formation of the corresponding aldehyde in a mixed-aqueous system. The detection limit of the probe is in the 10-8M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non-polar to polar, the emission band of TAM largely red-shifted. Moreover, the probe shows an excellent performance in real-life application in detecting OCl- in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl- were studied by DFT and TDDFT computational calculations. A new visible‐light‐excitable fluorescence ratiometric probe for OCl− has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The structure of the dye was confirmed by single‐crystal X‐ray analysis. It behaves as a highly selective and sensitive probe for OCl− over other analytes with a fast response time (∼100 s). OCl− reacts with the probe leading to the formation of the corresponding aldehyde in a mixed‐aqueous system. The detection limit of the probe is in the 10−8 M range. The probe (TAM) also exhibits solvatofluorochromism. Changing the solvent from non‐polar to polar, the emission band of TAM largely red‐shifted. Moreover, the probe shows an excellent performance in real‐life application in detecting OCl− in human blood cells. The experimentally observed changes in the structure and electronic properties of the probe after reaction with OCl− were studied by DFT and TDDFT computational calculations. Green means danger! A new triphenyl amine‐diaminomaleonitrile‐based probe was synthesized. This probe acts as a polarity probe with a strong positive emission solvatofluorochromism. It exclusively detects OCl− in a ratiometric manner in a mixed aqueous system with a detection limit of about 10−8 M. Moreover, it can detect OCl− in vivo in human blood cells. |
| Author | Bhattacharyya, Maitree Fun, Hoong-Kun Das, Sangita Aich, Krishnendu Pakhira, Bholanath Ghoshal, Kakali Sarkar, Sabyasachi Goswami, Shyamaprosad Quah, Ching Kheng |
| Author_xml | – sequence: 1 givenname: Shyamaprosad surname: Goswami fullname: Goswami, Shyamaprosad email: spgoswamical@yahoo.com organization: Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah-711103 (India) – sequence: 2 givenname: Krishnendu surname: Aich fullname: Aich, Krishnendu organization: Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah-711103 (India) – sequence: 3 givenname: Sangita surname: Das fullname: Das, Sangita organization: Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah-711103 (India) – sequence: 4 givenname: Bholanath surname: Pakhira fullname: Pakhira, Bholanath organization: Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah-711103 (India) – sequence: 5 givenname: Kakali surname: Ghoshal fullname: Ghoshal, Kakali organization: Department of Biochemistry, University of Calcutta, Kolkata-700019 (India) – sequence: 6 givenname: Ching Kheng surname: Quah fullname: Quah, Ching Kheng organization: X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang (Malaysia) – sequence: 7 givenname: Maitree surname: Bhattacharyya fullname: Bhattacharyya, Maitree organization: Department of Biochemistry, University of Calcutta, Kolkata-700019 (India) – sequence: 8 givenname: Hoong-Kun surname: Fun fullname: Fun, Hoong-Kun organization: X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang (Malaysia) – sequence: 9 givenname: Sabyasachi surname: Sarkar fullname: Sarkar, Sabyasachi organization: Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah-711103 (India) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25605132$$D View this record in MEDLINE/PubMed |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | ratiometric hypochlorite sensors solvatofluorochromism fluorescent probes blood-cell imaging |
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| Snippet | A new visible‐light‐excitable fluorescence ratiometric probe for OCl− has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The... A new visible‐light‐excitable fluorescence ratiometric probe for OCl − has been developed based on a triphenylamine‐diamiomaleonitrile (TAM) moiety. The... A new visible-light-excitable fluorescence ratiometric probe for OCl(-) has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The... A new visible-light-excitable fluorescence ratiometric probe for OCl- has been developed based on a triphenylamine-diamiomaleonitrile (TAM) moiety. The... |
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| SubjectTerms | Amines - chemistry Blood blood-cell imaging Chemistry Crystallography Erythrocytes - chemistry Fluorescent Dyes - chemistry fluorescent probes Humans hypochlorite Hypochlorous Acid - chemistry Models, Molecular Molecular Structure ratiometric sensors solvatofluorochromism |
| Title | A Triphenyl Amine-Based Solvatofluorochromic Dye for the Selective and Ratiometric Sensing of OCl− in Human Blood Cells |
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