Synthesis and Spectroscopic Characterization of 1,8-Naphthalimide Derived "Super" Photoacids
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| Publication date | 2015 |
| Journal | The journal of Physical Chemistry. B |
| Volume | Issue number | 119 | 6 |
| Pages (from-to) | 2515-2524 |
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| Abstract |
The ground- and excited-state acid-base properties of three novel naphthalimide-based "super" photoacids were studied using steady-state and time-resolved spectroscopy. The compds. exhibit pKa = 8.8-8.0 and pK*a = -1.2 to -1.9. The decrease in both ground- and excited-state pKa is achieved by attachment of an electron withdrawing group (sulfonate) on the arom. system. All compds. are deprotonated upon excitation in alcs. and DMSO. Good correlation is established between the pK*a and the ratio of the neutral and anion emission intensities in a certain solvent. The excited-state intermol. proton transfer to solvent (H2O and DMSO) is explained by a two-step model. In the first step, short-range proton transfer takes place, resulting in the formation of a contact ion pair. Free ion pairs are formed in the diffusion controlled second step.
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| Document type | Article |
| Note | - In Special Issue: Photoinduced Proton Transfer in Chemistry and Biology Symposium. - With supporting information |
| Language | English |
| Published at | https://doi.org/10.1021/jp508334s |
| Downloads |
Synthesis and Spectroscopic Characterization
(Final published version)
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