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 language | English |
|---|---|
| Pages (from-to) | 1559-1564 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society, Perkin Transactions 2 |
| Issue number | 9 |
| State | Published - 1 Dec 1992 |
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Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons. / Bissell, Richard A.; Calle, Emilio; De Silva, A. Prasanna; Desilva, Saliya; Gunaratne, H. Q.Nimal; Habib-Jiwan, Jean Louis; Peiris, S. L.Annesley; Rupasinghe, R. A.D.Dayasiri; Samarasinghe, T. K.Shantha D.; Sandanayake, K. R.A.Samankumara; Soumillion, Jean Philippe.
In: Journal of the Chemical Society, Perkin Transactions 2, No. 9, 01.12.1992, p. 1559-1564.Research output: Contribution to journal › Article
TY - JOUR
T1 - Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons
AU - Bissell, Richard A.
AU - Calle, Emilio
AU - De Silva, A. Prasanna
AU - Desilva, Saliya
AU - Gunaratne, H. Q.Nimal
AU - Habib-Jiwan, Jean Louis
AU - Peiris, S. L.Annesley
AU - Rupasinghe, R. A.D.Dayasiri
AU - Samarasinghe, T. K.Shantha D.
AU - Sandanayake, K. R.A.Samankumara
AU - Soumillion, Jean Philippe
PY - 1992/12/1
Y1 - 1992/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049066860&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049066860
SP - 1559
EP - 1564
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 1472-779X
IS - 9
ER -