Luminescence and Charge-transfer .2. Aminomethyl Anthracene-derivatives As Fluorescent Pet (photoinduced Electron-transfer) Sensors for Protons
(1992) Royal Society of Chemistry. Journal: Perkin Transactions 2 — n° 9, p. 1559-1564 (1992)
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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 pK(a) 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 10(10)-10(11) s-1, with the diamines 23 and 24b exhibiting the faster rates.
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Bissell, RA., Calle, E., Desilva, AP., Desilva, SA., Gunaratne, HQN., Habibjiwan, JL., Peiris, SLA., Rupasinghe, RADD., Samarasinghe, TKSD., Sandanayake, KRAS., & Soumillion, J.-P. (1992). Luminescence and Charge-transfer .2. Aminomethyl Anthracene-derivatives As Fluorescent Pet (photoinduced Electron-transfer) Sensors for Protons. Royal Society of Chemistry. Journal: Perkin Transactions 2, 9, 1559-1564. https://doi.org/10.1039/p29920001559 (Original work published 1992)