Buckyball as an Electron Donor in a Dyad of C60 and Xanthene Dye

Haruka Kano, Kyohei Matsuo, Hironobu Hayashi, Kosaku Kato, Akira Yamakata, Hiroko Yamada, Naoki Aratani

Research output: Contribution to journalArticlepeer-review

Abstract

We successfully achieved the synthesis of C60-xanthlium, X60_NTf2, where fullerene is an electron donor and xanthlium is an electron acceptor. When the precursor compound X60-OH was excited at 550 nm, the C60 emission was observed at 715 nm. On the other hand, the fluorescence of X60_NTf2 was completely quenched under the same conditions, suggesting that photo-induced intramolecular electron transfer (ET) occurred from the singlet excited state of C60. The electrochemical measurement proved that the X60_NTf2 is exothermically possible of ET reaction from 1C60* to xanthylium to form C60.+. Density functional theory (DFT) calculations support the acceptor ability of the xanthylium by showing that the coefficients of the lowest unoccupied molecular orbital (LUMO) were on xanthene moiety. This is a well-arranged model compound to investigate the properties of transiently generated fullerene radical cations.

Original languageEnglish
Pages (from-to)3377-3381
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number23
DOIs
Publication statusPublished - Jun 21 2021
Externally publishedYes

Keywords

  • Electron donor
  • Electron transfer
  • Fullerene
  • Fullerene cation
  • Xanthene dye

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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