Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach

Beena Varghese; Saleh N. Al-Busafi; Fakhr Eldin O. Suliman; Salma M.Z. Al-Kindy

doi:10.1016/j.saa.2016.09.047

Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach

Beena Varghese, Saleh N. Al-Busafi, Fakhr Eldin O. Suliman^*, Salma M.Z. Al-Kindy

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

The modulation in the photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP), when it drifts from bulk water into the nanocages of aqueous cyclodextrin solutions was investigated. The intramolecular charge transfer (ICT) fluorescence band intensity was found to increase with a blue shift in the presence of cyclodextrins. The results from ¹H NMR and ¹H[sbnd]H COSY NMR spectral analysis clearly points out the position of pyrazoline ring inside the cavity and its role in complexation process. A quantitative assessment of the emission intensity data on Benesi-Hildebrand (B-H) equation along with ESI-MS spectra reveals the probable stoichiometry of NPCP-CD complexes. Molecular docking and molecular dynamics studies were conducted for β/γ cyclodextrin associated inclusion complexes of NPCP. The results obtained by computational studies are in good relation with the data obtained through experimental methods and both ascertain the encapsulation of NPCP into cyclodextrins.

Original language	English
Pages (from-to)	383-389
Number of pages	7
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	173
DOIs	https://doi.org/10.1016/j.saa.2016.09.047
Publication status	Published - Feb 15 2017

Keywords

Complexation
Cyclodextrins
ESIMS
Fluorescence
Molecular modeling
NMR
Pyrazoline dye

ASJC Scopus subject areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

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Varghese, B., Al-Busafi, S. N., Suliman, F. E. O., & Al-Kindy, S. M. Z. (2017). Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 173, 383-389. https://doi.org/10.1016/j.saa.2016.09.047

Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach. / Varghese, Beena; Al-Busafi, Saleh N.; Suliman, Fakhr Eldin O. et al.
In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. 173, 15.02.2017, p. 383-389.

Research output: Contribution to journal › Article › peer-review

Varghese, B, Al-Busafi, SN , Suliman, FEO & Al-Kindy, SMZ 2017, 'Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach', Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, vol. 173, pp. 383-389. https://doi.org/10.1016/j.saa.2016.09.047

Varghese B, Al-Busafi SN , Suliman FEO, Al-Kindy SMZ. Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2017 Feb 15;173:383-389. doi: 10.1016/j.saa.2016.09.047

Varghese, Beena ; Al-Busafi, Saleh N. ; Suliman, Fakhr Eldin O. et al. / Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities : A detailed insight via experimental and theoretical approach. In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2017 ; Vol. 173. pp. 383-389.

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abstract = "The modulation in the photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP), when it drifts from bulk water into the nanocages of aqueous cyclodextrin solutions was investigated. The intramolecular charge transfer (ICT) fluorescence band intensity was found to increase with a blue shift in the presence of cyclodextrins. The results from 1H NMR and 1H[sbnd]H COSY NMR spectral analysis clearly points out the position of pyrazoline ring inside the cavity and its role in complexation process. A quantitative assessment of the emission intensity data on Benesi-Hildebrand (B-H) equation along with ESI-MS spectra reveals the probable stoichiometry of NPCP-CD complexes. Molecular docking and molecular dynamics studies were conducted for β/γ cyclodextrin associated inclusion complexes of NPCP. The results obtained by computational studies are in good relation with the data obtained through experimental methods and both ascertain the encapsulation of NPCP into cyclodextrins.",

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Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach

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