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 Desilva, 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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Protons
Charge transfer
Luminescence
Derivatives
Electrons
Methylamines
Sensors
Fluorescence
Diamines
Quantum yield
Phase shift
Ether
Amines
Rate constants
Electric fields
anthracene

Cite this

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. / Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons. In: Journal of the Chemical Society, Perkin Transactions 2. 1992 ; No. 9. pp. 1559-1564.
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title = "Luminescence and charge transfer. Part 2. Aminomethyl anthracene derivatives as fluorescent PET (Photoinduced Electron Transfer) sensors for protons",
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.",
author = "Bissell, {Richard A.} and Emilio Calle and {De Silva}, {A. Prasanna} and Saliya Desilva and Gunaratne, {H. Q.Nimal} and Habib-Jiwan, {Jean Louis} and Peiris, {S. L.Annesley} and Rupasinghe, {R. A.D.Dayasiri} and Samarasinghe, {T. K.Shantha D.} and Sandanayake, {K. R.A.Samankumara} and Soumillion, {Jean Philippe}",
year = "1992",
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pages = "1559--1564",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
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Bissell, RA, Calle, E, De Silva, AP, Desilva, S, Gunaratne, HQN, Habib-Jiwan, JL, Peiris, SLA, Rupasinghe, RADD, Samarasinghe, TKSD, Sandanayake, KRAS & Soumillion, JP 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, no. 9, pp. 1559-1564.

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 journalArticleResearchpeer-review

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.

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