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Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative
optical absorption spectra
polarizable continuum model (PCM)
fluorescence spectra
solvatochromism
DFT and TDDFT calculations
annulated heteroazulene dyes
Paper introduces new heteroazulene derivative, 10-methoxy-6-methyl-6 H -5,6,7-triazadibenzo[ f,h ] naphtho[3,2,1- cd ]azulene (MMTNA), including chemical aspects of its synthesis likewise optical absorption and fl uorescence spectra measured in several organic solvents of different polarity. The obtained experimental results are subjected to the quantum-chemical analysis based on DFT/TDDFT/PCM calculations at the B3LYP/6-31 þ G(d,p) level of theory. MMTNA demonstrates insigni fi cant sol- vatochromism of both fi rst absorption and fl uorescence bands caused mainly by a weakly polar feature of its ground and lowest excited states. Despite this the emission bands appears to be considerably red shifted with respect to relevant fi rst absorption bands resulting thus to a substantial Stokes shift. Its origin is dominated by the conformational relaxation in the excited state whereas the solvent relaxation has practically no in fl uence on the emission spectra. Low sensitivity to the host environment makes MMTNA dye perspective for a number of applications, particularly in those cases when a high stability of the emission wavelength (color) is demanded.
dc.abstract.en | Paper introduces new heteroazulene derivative, 10-methoxy-6-methyl-6 H -5,6,7-triazadibenzo[ f,h ] naphtho[3,2,1- cd ]azulene (MMTNA), including chemical aspects of its synthesis likewise optical absorption and fl uorescence spectra measured in several organic solvents of different polarity. The obtained experimental results are subjected to the quantum-chemical analysis based on DFT/TDDFT/PCM calculations at the B3LYP/6-31 þ G(d,p) level of theory. MMTNA demonstrates insigni fi cant sol- vatochromism of both fi rst absorption and fl uorescence bands caused mainly by a weakly polar feature of its ground and lowest excited states. Despite this the emission bands appears to be considerably red shifted with respect to relevant fi rst absorption bands resulting thus to a substantial Stokes shift. Its origin is dominated by the conformational relaxation in the excited state whereas the solvent relaxation has practically no in fl uence on the emission spectra. Low sensitivity to the host environment makes MMTNA dye perspective for a number of applications, particularly in those cases when a high stability of the emission wavelength (color) is demanded. | pl |
dc.affiliation | Wydział Chemii : Zakład Chemii Fizycznej i Elektrochemii | pl |
dc.contributor.author | Gąsiorski, Paweł | pl |
dc.contributor.author | Danel, Krzysztof S. | pl |
dc.contributor.author | Matusiewicz, Marek | pl |
dc.contributor.author | Uchacz, Tomasz - 162425 | pl |
dc.contributor.author | Kityk, Andriy V. | pl |
dc.date.accessioned | 2015-09-04T07:07:51Z | |
dc.date.available | 2015-09-04T07:07:51Z | |
dc.date.issued | 2012 | pl |
dc.description.number | 1-3 | pl |
dc.description.physical | 1538-1543 | pl |
dc.description.points | 45 | pl |
dc.description.volume | 93 | pl |
dc.identifier.doi | 10.1016/j.dyepig.2011.07.014 | pl |
dc.identifier.eissn | 1873-3743 | pl |
dc.identifier.issn | 0143-7208 | pl |
dc.identifier.uri | http://ruj.uj.edu.pl/xmlui/handle/item/15339 | |
dc.language | eng | pl |
dc.language.container | eng | pl |
dc.rights.licence | Bez licencji otwartego dostępu | |
dc.subject.en | optical absorption spectra | pl |
dc.subject.en | polarizable continuum model (PCM) | pl |
dc.subject.en | fluorescence spectra | pl |
dc.subject.en | solvatochromism | pl |
dc.subject.en | DFT and TDDFT calculations | pl |
dc.subject.en | annulated heteroazulene dyes | pl |
dc.subtype | Article | pl |
dc.title | Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative | pl |
dc.title.journal | Dyes and Pigments | pl |
dc.type | JournalArticle | pl |
dspace.entity.type | Publication |