Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine): singlet oxygen generating oligomers

Neetika Singh; Sumit Singh; S. M. Ashraf; Ufana Riaz

doi:10.1007/s00396-020-04707-3

Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine): singlet oxygen generating oligomers

Neetika Singh, Sumit Singh, S. M. Ashraf, Ufana Riaz

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

6 Scopus citations

Abstract

The present work reports microwave-assisted polymerization of 1,4-benzoquinone with ortho-phenylenediamine for the effective generation of singlet oxygen (¹O₂). The oligomeric structures were confirmed by the experimental IR, ¹H-NMR, ultraviolet-visible and TEM analyses. The theoretical IR and UV data were computed using DFT/B3LYP method with 6-311G basis set, and the ¹H-NMR spectra were computed by gauge-independent atomic orbital (GIAO) method. The experimental IR, ¹H-NMR, and UV studies were found to be in close agreement with the experimental investigations. The TEM studies confirmed the formation of mixed morphology consisting of cluster of fused particles joined together to form entangled chains. ¹O₂ generation studies revealed that the oligomer containing 70% benzoquinone content exhibited the highest quantum yield value of 0.057. These results hold promise for utilization of these oligomers as photosensitive probes applicable in photodynamic therapy for the treatment of various infectious diseases.

Original language	English
Pages (from-to)	1443-1453
Number of pages	11
Journal	Colloid and Polymer Science
Volume	298
Issue number	10
DOIs	https://doi.org/10.1007/s00396-020-04707-3
State	Published - 1 Oct 2020
Externally published	Yes

Keywords

Fluorescence
H-NMR
Morphology
Oligomer
Singlet oxygen

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Polymers and Plastics
Colloid and Surface Chemistry
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s00396-020-04707-3

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title = "Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine): singlet oxygen generating oligomers",

abstract = "The present work reports microwave-assisted polymerization of 1,4-benzoquinone with ortho-phenylenediamine for the effective generation of singlet oxygen (1O2). The oligomeric structures were confirmed by the experimental IR, 1H-NMR, ultraviolet-visible and TEM analyses. The theoretical IR and UV data were computed using DFT/B3LYP method with 6-311G basis set, and the 1H-NMR spectra were computed by gauge-independent atomic orbital (GIAO) method. The experimental IR, 1H-NMR, and UV studies were found to be in close agreement with the experimental investigations. The TEM studies confirmed the formation of mixed morphology consisting of cluster of fused particles joined together to form entangled chains. 1O2 generation studies revealed that the oligomer containing 70% benzoquinone content exhibited the highest quantum yield value of 0.057. These results hold promise for utilization of these oligomers as photosensitive probes applicable in photodynamic therapy for the treatment of various infectious diseases.",

keywords = "Fluorescence, H-NMR, Morphology, Oligomer, Singlet oxygen",

author = "Neetika Singh and Sumit Singh and Ashraf, {S. M.} and Ufana Riaz",

note = "Funding Information: Neetika Singh wishes to acknowledge the RGNF-SRF UGC, India, for providing senior research fellowship. The authors wish to acknowledge the sophisticated analytical instrumentation facility (SAIF) at Jamia Millia Islamia (JMI), New Delhi, India, for carrying out the TEM analysis. Publisher Copyright: {\textcopyright} 2020, Springer-Verlag GmbH Germany, part of Springer Nature.",

year = "2020",

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doi = "10.1007/s00396-020-04707-3",

language = "English",

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TY - JOUR

T1 - Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine)

T2 - singlet oxygen generating oligomers

AU - Singh, Neetika

AU - Singh, Sumit

AU - Ashraf, S. M.

AU - Riaz, Ufana

N1 - Funding Information: Neetika Singh wishes to acknowledge the RGNF-SRF UGC, India, for providing senior research fellowship. The authors wish to acknowledge the sophisticated analytical instrumentation facility (SAIF) at Jamia Millia Islamia (JMI), New Delhi, India, for carrying out the TEM analysis. Publisher Copyright: © 2020, Springer-Verlag GmbH Germany, part of Springer Nature.

PY - 2020/10/1

Y1 - 2020/10/1

N2 - The present work reports microwave-assisted polymerization of 1,4-benzoquinone with ortho-phenylenediamine for the effective generation of singlet oxygen (1O2). The oligomeric structures were confirmed by the experimental IR, 1H-NMR, ultraviolet-visible and TEM analyses. The theoretical IR and UV data were computed using DFT/B3LYP method with 6-311G basis set, and the 1H-NMR spectra were computed by gauge-independent atomic orbital (GIAO) method. The experimental IR, 1H-NMR, and UV studies were found to be in close agreement with the experimental investigations. The TEM studies confirmed the formation of mixed morphology consisting of cluster of fused particles joined together to form entangled chains. 1O2 generation studies revealed that the oligomer containing 70% benzoquinone content exhibited the highest quantum yield value of 0.057. These results hold promise for utilization of these oligomers as photosensitive probes applicable in photodynamic therapy for the treatment of various infectious diseases.

AB - The present work reports microwave-assisted polymerization of 1,4-benzoquinone with ortho-phenylenediamine for the effective generation of singlet oxygen (1O2). The oligomeric structures were confirmed by the experimental IR, 1H-NMR, ultraviolet-visible and TEM analyses. The theoretical IR and UV data were computed using DFT/B3LYP method with 6-311G basis set, and the 1H-NMR spectra were computed by gauge-independent atomic orbital (GIAO) method. The experimental IR, 1H-NMR, and UV studies were found to be in close agreement with the experimental investigations. The TEM studies confirmed the formation of mixed morphology consisting of cluster of fused particles joined together to form entangled chains. 1O2 generation studies revealed that the oligomer containing 70% benzoquinone content exhibited the highest quantum yield value of 0.057. These results hold promise for utilization of these oligomers as photosensitive probes applicable in photodynamic therapy for the treatment of various infectious diseases.

KW - Fluorescence

KW - H-NMR

KW - Morphology

KW - Oligomer

KW - Singlet oxygen

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M3 - Article

AN - SCOPUS:85088259685

SN - 0303-402X

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EP - 1453

JO - Colloid and Polymer Science

JF - Colloid and Polymer Science

IS - 10

ER -

Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine): singlet oxygen generating oligomers

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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