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Dehydrogenation induced inhibition of intramolecular charge transfer in substituted pyrazoline analogues

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Abstract

The detailed photophysics of (E)-1,5-diphenyl-3-styryl-4,5-dihydro-1H-pyrazole (DSDP) and (E)-1,5-diphenyl-3-styryl-1H-pyrazole (DSP) has been investigated and compared to demonstrate the drastic modification of the photophysics upon dehydrogenation of the pyrazoline ring. While DSDP gives dual absorption and dual emission bands corresponding to the locally excited (LE) and the intramolecular charge transfer (ICT) species, DSP yields single absorption and emission bands for the locally excited species only. Comparative steady state and time resolved fluorometric studies reveal that aromatization of the pyrazoline ring inhibits the formation of the ICT species. Quantum chemical calculations corroborate and rationalize the inhibition of the ICT process upon aromatization through depiction of the differential electronic distributions in the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of the two fluorophores.

Graphical abstract: Dehydrogenation induced inhibition of intramolecular charge transfer in substituted pyrazoline analogues

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Publication details

The article was received on 20 Feb 2017, accepted on 03 Apr 2017 and first published on 06 Apr 2017


Article type: Paper
DOI: 10.1039/C7CP01121K
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    Dehydrogenation induced inhibition of intramolecular charge transfer in substituted pyrazoline analogues

    P. Kundu, D. Banerjee, G. Maiti and N. Chattopadhyay, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP01121K

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