Intramolecular charge transfer of a push–pull chromophore with restricted internal rotation of an electron donor

Lee, Sebok; Jen, Myungsam; Lee, Gisang; Jang, Taehyung; Pang, Yoonsoo

doi:10.1039/d1cp05541k

Cited by 4 publications

(3 citation statements)

References 80 publications

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“…This behaviour is a characteristic property in push-pull systems due to the intramolecular charge transfer (ICT) phenomenon. In ICT, charge redistribution occurs from the electron donor to the acceptor system [44][45][46][47].…”

Section: Absorption and Uorescence Spectral Studiesmentioning

confidence: 99%

Solvent polarity induces significant bathochromic shift on (4Z,4'Z)-4,4'- (((phenylazanediyl) bis (4,1-phenylene)) bis (methaneylylidene)) bis (2- phenyloxazol-5(4H)-one)

Gowri

Ranganathan

Ramanathan

2023

Preprint

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A new environment-sensitive fluorescent probe (4Z, 4ʹZ)-4, 4ʹ-(((phenylazanediyl) bis (4, 1-phenylene)) bis (methanylylidene)) bis (2-phenyloxazol-5(4H)-one) (PPMP) is reported. PPMP emits light in the 508 to 644 nm region, making it a workable fluorescent probe. The molecule exhibits a substantial bathochromic shift with changing solvent polarity. The results are analyzed in terms of Onsager's reaction field theory. Bilot–Kawski, Lippert–Mataga, Bakhshiev, and Reichardt correlations are used to estimate the ground and excited state dipole moments. The results show that the predicted dipole moment of the excited state is significantly greater than that of the ground state. Gas phase quantum mechanical calculations based on density functional theory support the experimental results. This remarkable stability in a polar solvent, of the excited state, compared to the ground state, causes a significant bathochromic shift.

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Section: Absorption and Uorescence Spectral Studiesmentioning

confidence: 99%

Solvent polarity induces significant bathochromic shift on (4Z,4'Z)-4,4'- (((phenylazanediyl) bis (4,1-phenylene)) bis (methaneylylidene)) bis (2- phenyloxazol-5(4H)-one)

Gowri

Ranganathan

Ramanathan

2023

Preprint

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“…The ICT dynamics of push–pull chromophores and molecular complexes have been extensively studied by numerous time-resolved spectroscopy and theoretical methods 4 , 16 – 26 . Most of these works focused on the photophysical properties, including absorption and emission, and the structural changes of the chromophores or complexes in the excited state such as the twist of electron donor or acceptor groups have been often suggested based on the changes in the electronic structures and theoretical simulations results 4 , 5 , 18 , 27 – 31 .…”

Section: Introductionmentioning

confidence: 99%

Twisted intramolecular charge transfer of nitroaromatic push–pull chromophores

Lee

Jen

Jang

et al. 2022

Sci Rep

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The structural changes during the intramolecular charge transfer (ICT) of nitroaromatic chromophores, 4-dimethylamino-4′-nitrobiphenyl (DNBP) and 4-dimethylamino-4′-nitrostilbene (DNS) were investigated by femtosecond stimulated Raman spectroscopy (FSRS) with both high spectral and temporal resolutions. The kinetically resolved Raman spectra of DNBP and DNS in the locally-excited and charge-transferred states of the S1 state appear distinct, especially in the skeletal vibrational modes of biphenyl and stilbene including ν8a and νC=C. The ν8a of two phenyls and the νC=C of the central ethylene group (only for stilbene), which are strongly coupled in the planar geometries, are broken with the twist of nitrophenyl group with the ICT. Time-resolved vibrational spectroscopy measurements and the time-dependent density functional theory simulations support the ultrafast ICT dynamics of 220–480 fs with the twist of nitrophenyl group occurring in the S1 state of the nitroaromatic chromophores. While the ICT of DNBP occurs via a barrier-less pathway, the ICT coordinates of DNS are strongly coupled to several low-frequency out-of-phase deformation modes relevant to the twist of the nitrophenyl group.

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“…Therefore, we proposed that the TICT behavior might be restricted in mixed water with poor solubility due to the aggregation of keto, further leading to enhanced K-FL. Thus, ESIPT and AIE are not mutually exclusive but together, which produce a fluorescent enhancement phenomenon owing to restricted intramolecular reversal (RIR) 28,34,[52][53][54] for aggregated HBO-pCH 3 .…”

mentioning

confidence: 99%

Spectroscopic and mechanistic insights into solvent mediated excited-state proton transfer and aggregation-induced emission: introduction of methyl group onto 2-(o-hydroxyphenyl)benzoxazole

Wang

Feng

et al. 2022

Phys. Chem. Chem. Phys.

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Intramolecular charge transfer of a push–pull chromophore with restricted internal rotation of an electron donor

Cited by 4 publications

References 80 publications

Solvent polarity induces significant bathochromic shift on (4Z,4'Z)-4,4'- (((phenylazanediyl) bis (4,1-phenylene)) bis (methaneylylidene)) bis (2- phenyloxazol-5(4H)-one)

Solvent polarity induces significant bathochromic shift on (4Z,4'Z)-4,4'- (((phenylazanediyl) bis (4,1-phenylene)) bis (methaneylylidene)) bis (2- phenyloxazol-5(4H)-one)

Twisted intramolecular charge transfer of nitroaromatic push–pull chromophores

Spectroscopic and mechanistic insights into solvent mediated excited-state proton transfer and aggregation-induced emission: introduction of methyl group onto 2-(o-hydroxyphenyl)benzoxazole

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