Experimental and theoretical studies of benzoquinone modified poly( ortho -phenylenediamine): singlet oxygen generating
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Experimental and theoretical studies of benzoquinone modified poly(ortho-phenylenediamine): singlet oxygen generating oligomers Neetika Singh 1 & Sumit Singh 1 & S. M. Ashraf 1 & Ufana Riaz 1 Received: 27 December 2019 / Revised: 26 May 2020 / Accepted: 10 July 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
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, ultravioletvisible 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 Oligomer . 1H-NMR . Singlet oxygen . Morphology . Fluorescence
Introduction In spite of the substantial improvement in drug discovery, molecular biology and oncology, cancer is considered to be one of the major causes of death worldwide [1, 2]. “Oxidative therapy” is one of the recently developed anticancer therapeutics which has gained significant attention [3]. As compared with normal cells, cancer cells have elevated levels of reactive oxygen species (ROS) such as 1O2, H2O2 and ●OH radicals and therefore experience immense oxidative stress [4–6]. Singlet oxygen (1O2) has been widely reported to be used in photodynamic therapy (PDT) for effectively targeting the cytotoxic cancer cells [7–9]. The literature survey reveals that various organic compounds have been functionalized to effectively generate 1O2 S. M. Ashraf is now retired Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00396-020-04707-3) contains supplementary material, which is available to authorized users. * Ufana Riaz [email protected]; [email protected] 1
Materials Research Laboratory, Department of Chemistry, Jamia Millia Islamia, New Delhi 110025, India
[10]. Ding and Han [10] reported the synthesis of novel metallo-phthalocyanine (MPc)-based conjugated microporous polymers (MPc-CMPs) as photosensitizers for the generation of 1O2. Jiang et al. [9] have utilized the Forster resonance energy transfer (FRET) strategy to design dual-emissive semiconducting polymer nanoparticle–based photosensitizers containing BODIPY derivatives and near-infrared phosphorescent iridium (III) complexes for amplified 1O2 generation. Grzechnik et al. [11] pr
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