Low-temperature spectra of the analogues of 10-hydroxybenzo[h]quinoline as an indication of barrierless ESIPT.

@article{Deperasiska2012LowtemperatureSO,
  title={Low-temperature spectra of the analogues of 10-hydroxybenzo[h]quinoline as an indication of barrierless ESIPT.},
  author={Irena Deperasińska and Daniel T. Gryko and Elena Karpiuk and Bolesław Kozankiewicz and Artur Makarewicz and Joanna Piechowska},
  journal={The journal of physical chemistry. A},
  year={2012},
  volume={116 49},
  pages={
          12049-55
        }
}
The absorption and fluorescence spectra of two analogues of 10-hydroxybenzo[h]quinoline (10-HBQ), namely, 1-hydroxy-7-methylbenzo[c]acridine (HMBA) and 4-hydroxybenzo[c]phenanthridine (HBPA), were studied in n-alkane matrices at 5 K. Considerable energy separation between the onsets of the spectra and broadening of the bands was an indication that intramolecular proton transfer (ESIPT) takes place at such a low temperature. DFT and ab initio methods were used to calculate the electronic… Expand
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References

SHOWING 1-10 OF 73 REFERENCES
Photophysics of 10-Hydroxybenzo[h]quinoline in Aqueous Solution
Various 7,8-benzoquinoline (BQ) derivatives have been synthesized and studied in order to determine the fluorescence species and dynamics of excited-state proton transfer (ESPT) ofExpand
Excited state intramolecular proton transfer in electron-rich and electron-poor derivatives of 10-hydroxybenzo[h]quinoline.
TLDR
On the basis of time-resolved measurements, proton transfer was found to be extremely fast with time constants in the range (0.08-0.45 ps) and some design patterns giving rise to NIR emission and large Stokes shifts were identified. Expand
Preparation of a family of 10-hydroxybenzo[h]quinoline analogues via a modified Sanford reaction and their excited state intramolecular proton transfer properties.
TLDR
This synthesis was compatible with diverse functionalities and worked for sterically hindered analogues as well as for compounds possessing electron-donating and electron-withdrawing substituents at various positions, and demonstrated excited-state intramolecular proton transfer (ESIPT). Expand
Excited-state intramolecular proton transfer (ESIPT) in 2-(2′-hydroxyphenyl)-oxazole and -thiazole
The azoles 2-(2 0 -hydroxyphenyl)oxazole (HPO) and 2-(2 0 -hydroxyphenyl)-4-methylthiazole (HPT) have been synthesised and studied in order to compare their photophysical characteristics. TheirExpand
12-hydroxy-1-azaperylene-limiting case of the ESIPT system: enol-keto tautomerization in S0 and S1 states.
TLDR
Observation of absorption and fluorescence of both tautomeric forms and lack of large Stokes shift offluorescence of the keto form classify HAP as the limiting case of the excited-state intramolecular proton transfer system. Expand
Mercury ions complexation with a series of heterocyclic derivatives of 3-hydroxychromone: spectral effects and prospects for ultrasensitive Hg2+ probing.
TLDR
High sensitivity to mercury of 2,5-diphenyloxazole-substituted 3-hydroxychromone was elucidated, allowing to detect Hg(2+) below the maximum permissible concentration for drinking water, which makes the compound a prospective basis for development of sensors for ultralow mercury concentration detection in water. Expand
Modulation of the ESIPT emission of benzothiazole type dye incorporated in silica-based hybrid materials.
TLDR
For the first time, a modulation in the ESIPT fluorescence emission was achieved, being correlated to the methyl organic content of the hybrid matrix. Expand
Excited-state intramolecular proton transfer of naphthalene-fused 2-(2'-hydroxyaryl)benzazole family.
TLDR
The excited-state dynamics of a new family of ESIPT molecules, 2-(2'-hydroxynaphthyl)benzazoles 1-3, are reported based on steady-state and time-resolved spectroscopy measurements, indicating that the introduction of a naphthalene ring increases the energy gap between the ground and excited states for the keto-tautomer despite the expansion of the aromatic ring. Expand
Bright, emission tunable fluorescent dyes based on imidazole and π-expanded imidazole
A diverse set of imidazole- and π-expanded imidazole derivatives displaying excited state intramolecular proton transfer (ESIPT) was designed and synthesized. The effect of structural variation onExpand
Photophysics of organic photostabilizers. Ab initio study of the excited-state deactivation mechanisms of 2-(2'-hydroxyphenyl)benzotriazole.
TLDR
The keto-type planar S(1) state reached by barrierless intramolecular hydrogen transfer is found to be unstable with respect to torsion and this photophysical pathway accounts for the remarkable photostability of the molecule. Expand
...
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4
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