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

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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
StatePublished - 1 Dec 1992

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Bissell, R. A., Calle, E., De Silva, A. P., De Silva, S. A., Gunaratne, H. Q. N., Habib-Jiwan, J. L., Peiris, S. L. A., Rupasinghe, R. A. D. D., Samarasinghe, T. K. S. D., Sandanayake, K. R. A. S., & Soumillion, J. P. (1992). Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons. Journal of the Chemical Society, Perkin Transactions 2, (9), 1559-1564.