Emissive Features of Perylene Diimide Derivative with β-Cyclodextrin: Probing the role of inter and intramolecular interactions.

Autor: Barooah N; Bhabha Atomic Research Centre, Radiation & Photochemistry Division, INDIA., Soni G; Bhabha Atomic Research Centre, Radiation & Photochemistry Division, INDIA., Ghosh R; Bhabha Atomic Research Centre, Radiation & Photochemistry Division, INDIA., Mohanty J; Bhabha Atomic Research Centre, Radiation & Photochemistry Division, INDIA., Bhasikuttan AC; Bhabha Atomic Research Centre, Radiation and Photochemistry Division, Trombay, 400085, Mumbai, INDIA.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2024 Dec 13, pp. e202401255. Date of Electronic Publication: 2024 Dec 13.
DOI: 10.1002/asia.202401255
Abstrakt: Perylene diimide (PDI) derivatives have been extensively explored as chromophoric dyes for functional organic materials. Here, the custom synthesized tyrosine appended perylene diimide (PDI-Tyr) derivative has shown strong aggregation in aqueous medium diminishing its emissive features, which was surpassed by the supramolecular interaction with β-cyclodextrin (β-CD). Complex formation between PDI-Tyr and β-CD, proposed from the absorption and emission studies, have been substantiated by the 1H-NMR, ITC and geometry optimization data. Time-resolved emission and transient absorption studies carried out on PDI-Tyr in the absence and presence of β-CD, revealed an excited state intramolecular charge transfer (ICT) process from the tyrosine moiety to the PDI core with a time constant of ~30 ps, and the same gets retarded on encapsulation of the tyrosine groups in the βCD:PDI-Tyr (2:1) complex and the kinetics slows down to ~480ps, reviving the emissive features. The absence of a long lifetime component and the lower emission enhancement in the monomeric condition as compared to the phenyl alanine (PDI-Phe) derivative, emphasizes the major role of the ICT process in PDI-Tyr, which subdue the features of intermolecular aggregation, establishing the tunability of the emissive properties with the customization of intra and intermolecular interactions.
(© 2024 Wiley‐VCH GmbH.)
Databáze: MEDLINE
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