Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative

2012
journal article
article
dc.abstract.enPaper 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.affiliationWydział Chemii : Zakład Chemii Fizycznej i Elektrochemiipl
dc.contributor.authorGąsiorski, Pawełpl
dc.contributor.authorDanel, Krzysztof S.pl
dc.contributor.authorMatusiewicz, Marekpl
dc.contributor.authorUchacz, Tomasz - 162425 pl
dc.contributor.authorKityk, Andriy V.pl
dc.date.accessioned2015-09-04T07:07:51Z
dc.date.available2015-09-04T07:07:51Z
dc.date.issued2012pl
dc.description.number1-3pl
dc.description.physical1538-1543pl
dc.description.points45pl
dc.description.volume93pl
dc.identifier.doi10.1016/j.dyepig.2011.07.014pl
dc.identifier.eissn1873-3743pl
dc.identifier.issn0143-7208pl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/15339
dc.languageengpl
dc.language.containerengpl
dc.rights.licencebez licencji
dc.subject.enoptical absorption spectrapl
dc.subject.enpolarizable continuum model (PCM)pl
dc.subject.enfluorescence spectrapl
dc.subject.ensolvatochromismpl
dc.subject.enDFT and TDDFT calculationspl
dc.subject.enannulated heteroazulene dyespl
dc.subtypeArticlepl
dc.titleSynthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivativepl
dc.title.journalDyes and Pigmentspl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.enpl
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.affiliationpl
Wydział Chemii : Zakład Chemii Fizycznej i Elektrochemii
dc.contributor.authorpl
Gąsiorski, Paweł
dc.contributor.authorpl
Danel, Krzysztof S.
dc.contributor.authorpl
Matusiewicz, Marek
dc.contributor.authorpl
Uchacz, Tomasz - 162425
dc.contributor.authorpl
Kityk, Andriy V.
dc.date.accessioned
2015-09-04T07:07:51Z
dc.date.available
2015-09-04T07:07:51Z
dc.date.issuedpl
2012
dc.description.numberpl
1-3
dc.description.physicalpl
1538-1543
dc.description.pointspl
45
dc.description.volumepl
93
dc.identifier.doipl
10.1016/j.dyepig.2011.07.014
dc.identifier.eissnpl
1873-3743
dc.identifier.issnpl
0143-7208
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/15339
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights.licence
bez licencji
dc.subject.enpl
optical absorption spectra
dc.subject.enpl
polarizable continuum model (PCM)
dc.subject.enpl
fluorescence spectra
dc.subject.enpl
solvatochromism
dc.subject.enpl
DFT and TDDFT calculations
dc.subject.enpl
annulated heteroazulene dyes
dc.subtypepl
Article
dc.titlepl
Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative
dc.title.journalpl
Dyes and Pigments
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations

* The migration of download and view statistics prior to the date of April 8, 2024 is in progress.

Views
3
Views per month
Views per city
Bayreuth
1

No access

No Thumbnail Available