A density functional study to choose the best fluorophore for photon-induced electron-transfer (PET) sensors

Abhijit Chatterjee, Toshishige M. Suzuki, Yukiko Takahashi, David A. Pacheco Tanaka

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)


Anthracenes bearing aliphatic or aromatic amino substituents, which behave as molecular sensors, have shown their potential to act as photoninduced electron-transfer (PET) systems. In this PET, the fluorophore moieties are responsible for electron release during protonation and deprotonation. The principle of hard and soft acids and bases (HSAB) deals with both intra- and intermolecular electron migration. It is possible to calculate the localized properties in terms of Fukui functions in the realm of density functional theory (DFT) and thus calculate and establish a numerical matchmaking procedure that will generate an a priori rule for choosing the fluorophore in terms of its activity. We calculated the localized properties for neutral, anionic, and cationic systems to trace the course of the efficiency. A qualitative scale is proposed in terms of the feasibility of intramolecular hydrogen bonding. To investigate the effect of the environment of the nitrogen atom on protonation going from mono- to diprotonated systems, we calculated the partial density of states and compared the activity sequence with reactivity indices. The results show that location of the nitrogen atom in an aromatic ring does not influence the PET, but for aliphatic chains it plays a role. Furthermore, the protonation/deprotonation scenario has been explained. The results show that the reactivity indices can be used as a suitable property for scaling the activity of fluorophore molecules for the PET process.

Original languageEnglish
Pages (from-to)3920-3929
Number of pages10
JournalChemistry - A European Journal
Issue number16
Publication statusPublished - 2003 Aug 18
Externally publishedYes


  • Density functional calculations
  • Donor-acceptor systems
  • Electron transfer
  • Reactivity indices
  • Sensors

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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