Photophysics of the 2-(2′-hydroxyphenyl)perimidine: On the fluorescence of the enol form

Catalán, Javier; Valle, Juan Carlos del; Claramunt, Rosa M.; Sanz, Dionísia; Dotor, Julio

doi:10.1016/0022-2313(96)00005-1

Cited by 69 publications

(22 citation statements)

References 20 publications

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“…The photophysics at the IMHB site in aromatic systems has gained particular attention because of its essential role in the functionality of so-called photostabilizers [11,12] which are in wide technical use for the protection of organic polymers against degradation by the UV components of the sunlight [13,14]. Also the characteristic four-level photophysical scheme of PT reaction allows almost complete exclusion of self-absorption (rupture of mirror image symmetry between absorption and emission spectra) whereby paving ways for its potential applications as proton transfer lasers [15,16], UV filters, light emitting diodes (LEDs) [17] and so forth.…”

Section: Introductionmentioning

confidence: 99%

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Paul

Guchhait

2011

Journal of Luminescence

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Section: Introductionmentioning

confidence: 99%

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Paul

Guchhait

2011

Journal of Luminescence

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“…(a) Absorption spectra of 2,10, 13, 14, 18,and 22 in DCM. (b) Absorption spectra of 7 in four solvents.…”

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confidence: 99%

Excited State Intramolecular Proton Transfer in Electron-Rich and Electron-Poor Derivatives of 10-Hydroxybenzo[h]quinoline

et al. 2012

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Eight previously inaccessible derivatives of 10-hydroxybenzo[h]quinoline were prepared via a straightforward strategy comprising formation of the benzo[h]quinoline skeleton followed by C-H acetoxylation at position 10. The occurrence of excited state intramolecular proton transfer (ESIPT) was detected in all cases since emission was observed only from the excited keto-tautomer. Studies on derivatives bearing both electron-donating and electron-withdrawing groups adjacent to the pyridine ring allowed us to identify some design patterns giving rise to NIR emission and large Stokes shifts. For a derivative of 10-hydroxybenzo[c]acridine, emission at 745 nm was observed, one of the lowest energy fluorescence ever reported for ESIPT system. 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).

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“…As observed for most of the perimidines, which either do not present luminescence or have very low emission intensities with quantum yield (Φ) of order of 10 –3 ‐10 –5 , the strongly conjugated perinones of the MP type did not emit , , , . However, the perinones of less extended conjugation, such as SP or IP , showed a remarkably strong emission with Φ ca.…”

Section: Resultsmentioning

confidence: 90%

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

et al. 2019

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Highly conjugated perinones were evaluated as proligands with [Ru(η 6 -arene)Cl 2 ] 2 precursors (arene = p-cymene or benzene). None of them, except itaco-perinone (IP) bearing one exocyclic methylene group, were able to form coordination compounds. Expected η 1 -coordination through the lone pair of the nitrogen or oxygen atoms of the perinone did not occur. Instead a deprotonation reaction involving the exocyclic methylene was observed and the corresponding [Ru(η 6 -arene)- [a] 3494 (η 3 -IP)Cl] complex was isolated in moderate yields. Mechanistic studies revealed that the base-promoted isomerization of itacoperinone to citraco-perinone prevented higher yields in the synthesis of the allylic complexes. Additionally, it was observed that IP can dimerize through the exocyclic methylene group, indicating high reactivity of this carbon-carbon double bond. Electronic absorption and emission properties of the perinones and organometallic compounds were studied.

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Photophysics of the 2-(2′-hydroxyphenyl)perimidine: On the fluorescence of the enol form

Cited by 69 publications

References 20 publications

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Excited State Intramolecular Proton Transfer in Electron-Rich and Electron-Poor Derivatives of 10-Hydroxybenzo[h]quinoline

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

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