Synthesis, spectroscopic characterization and photophysics of a novel environmentally sensitive dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline

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Abstract

Synthesis and photophysical properties of a novel pyrazoline - containing fluorophore, 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP) A, and its proline derivative (NPCP-P) B are presented in this work. The highlight of this fluorescent dye is that, it can be prepared from available starting material via two synthetic steps, easily converted to the corresponding amide derivative by in situ nucleophilic acyl substitution of the corresponding acid chloride, and its purification by simple chromatographic techniques. The structures of the new compounds were verified using various spectroscopic tools. Furthermore, photophysical properties of the new fluorophores were studied and interesting solvatochromic behaviour was observed. Due to the presence of proton acceptor linked to the fluorophore, NPCP displays pH-sensitive absorption and fluorescence emission. The interaction of NPCP and NPCP-P with various micelles has been studied by steady state fluorescence. All results reflect the importance of the medium effect on the analytical application of NPCP as a potential fluorescent label for derivatization of analytes having amine (-NH2) group. Theoretical calculations were performed for both compounds using time dependent density functional theory (TD-DFT) at B3LYP/6-31G(d, p) level. The calculations indicate that the exited state dipole moments are larger than those of the ground state in line with the experimental findings.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalJournal of Luminescence
Volume159
DOIs
Publication statusPublished - 2015

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Fluorophores
Coloring Agents
Fluorescence
dyes
fluorescence
Micelles
synthesis
Fluorescent Dyes
Proline
purification
Amides
amides
Derivatives
Amines
Protons
Chlorides
micelles
amines
dipole moments
chlorides

Keywords

  • Charge-transfer character
  • Fluorescence
  • Pyrazoline
  • Solvent effect
  • Synthesis
  • TD-DFT

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Chemistry(all)
  • Biochemistry
  • Biophysics

Cite this

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title = "Synthesis, spectroscopic characterization and photophysics of a novel environmentally sensitive dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline",
abstract = "Synthesis and photophysical properties of a novel pyrazoline - containing fluorophore, 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP) A, and its proline derivative (NPCP-P) B are presented in this work. The highlight of this fluorescent dye is that, it can be prepared from available starting material via two synthetic steps, easily converted to the corresponding amide derivative by in situ nucleophilic acyl substitution of the corresponding acid chloride, and its purification by simple chromatographic techniques. The structures of the new compounds were verified using various spectroscopic tools. Furthermore, photophysical properties of the new fluorophores were studied and interesting solvatochromic behaviour was observed. Due to the presence of proton acceptor linked to the fluorophore, NPCP displays pH-sensitive absorption and fluorescence emission. The interaction of NPCP and NPCP-P with various micelles has been studied by steady state fluorescence. All results reflect the importance of the medium effect on the analytical application of NPCP as a potential fluorescent label for derivatization of analytes having amine (-NH2) group. Theoretical calculations were performed for both compounds using time dependent density functional theory (TD-DFT) at B3LYP/6-31G(d, p) level. The calculations indicate that the exited state dipole moments are larger than those of the ground state in line with the experimental findings.",
keywords = "Charge-transfer character, Fluorescence, Pyrazoline, Solvent effect, Synthesis, TD-DFT",
author = "Beena Varghese and Al-Busafi, {Saleh N.} and Suliman, {FakhrEldin O.} and Al-Kindy, {Salma M Z}",
year = "2015",
doi = "10.1016/j.jlumin.2014.10.045",
language = "English",
volume = "159",
pages = "9--16",
journal = "Journal of Luminescence",
issn = "0022-2313",
publisher = "Elsevier",

}

TY - JOUR

T1 - Synthesis, spectroscopic characterization and photophysics of a novel environmentally sensitive dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline

AU - Varghese, Beena

AU - Al-Busafi, Saleh N.

AU - Suliman, FakhrEldin O.

AU - Al-Kindy, Salma M Z

PY - 2015

Y1 - 2015

N2 - Synthesis and photophysical properties of a novel pyrazoline - containing fluorophore, 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP) A, and its proline derivative (NPCP-P) B are presented in this work. The highlight of this fluorescent dye is that, it can be prepared from available starting material via two synthetic steps, easily converted to the corresponding amide derivative by in situ nucleophilic acyl substitution of the corresponding acid chloride, and its purification by simple chromatographic techniques. The structures of the new compounds were verified using various spectroscopic tools. Furthermore, photophysical properties of the new fluorophores were studied and interesting solvatochromic behaviour was observed. Due to the presence of proton acceptor linked to the fluorophore, NPCP displays pH-sensitive absorption and fluorescence emission. The interaction of NPCP and NPCP-P with various micelles has been studied by steady state fluorescence. All results reflect the importance of the medium effect on the analytical application of NPCP as a potential fluorescent label for derivatization of analytes having amine (-NH2) group. Theoretical calculations were performed for both compounds using time dependent density functional theory (TD-DFT) at B3LYP/6-31G(d, p) level. The calculations indicate that the exited state dipole moments are larger than those of the ground state in line with the experimental findings.

AB - Synthesis and photophysical properties of a novel pyrazoline - containing fluorophore, 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP) A, and its proline derivative (NPCP-P) B are presented in this work. The highlight of this fluorescent dye is that, it can be prepared from available starting material via two synthetic steps, easily converted to the corresponding amide derivative by in situ nucleophilic acyl substitution of the corresponding acid chloride, and its purification by simple chromatographic techniques. The structures of the new compounds were verified using various spectroscopic tools. Furthermore, photophysical properties of the new fluorophores were studied and interesting solvatochromic behaviour was observed. Due to the presence of proton acceptor linked to the fluorophore, NPCP displays pH-sensitive absorption and fluorescence emission. The interaction of NPCP and NPCP-P with various micelles has been studied by steady state fluorescence. All results reflect the importance of the medium effect on the analytical application of NPCP as a potential fluorescent label for derivatization of analytes having amine (-NH2) group. Theoretical calculations were performed for both compounds using time dependent density functional theory (TD-DFT) at B3LYP/6-31G(d, p) level. The calculations indicate that the exited state dipole moments are larger than those of the ground state in line with the experimental findings.

KW - Charge-transfer character

KW - Fluorescence

KW - Pyrazoline

KW - Solvent effect

KW - Synthesis

KW - TD-DFT

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