Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (photoinduced electron transfer) sensors for protons
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- Vol. 23 (9) , 1559-1564
- https://doi.org/10.1039/p29920001559
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.Keywords
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