Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons

Richard A. Bissell*, Emilio Calle, A. Prasanna De Silva, Saliya A. De Silva, H. Q.Nimal Gunaratne, Jean Louis Habib-Jiwan, S. L.Annesley Peiris, R. A.D.Dayasiri Rupasinghe, T. K.Shantha D. Samarasinghe, K. R.A.Samankumara Sandanayake, Jean Philippe Soumillion

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

104 Citations (Scopus)

Abstract

The importance of the modular structure 'fluor-spacer-amine' is pointed out for the design of fluorescent molecular sensors for pH according to the principle of photoinduced electron transfer (PET). Anthracen-9-yl methylamines (24) and some azacrown ether analogues (15 and 23) are examined in this context. They show pH-dependent fluorescence quantum yields describable by eqn. (5) while all other electronic spectral parameters remain essentially pH-invariant. The range of pKa values of these sensors are understandable in terms of macrocyclic effects and the transmission of electric fields across the anthracene short axis. Phase-shift fluorometric determination of the fluorescence lifetimes of these sensors allows the calculation of the rate constant of PET in their proton-free form to be 1010-1011 s-1, with the diamines 23 and 24b exhibiting the faster rates.

Original languageEnglish
Pages (from-to)1559-1564
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number9
DOIs
Publication statusPublished - 1992

Bibliographical note

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Chemistry(all)

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