Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Cationic biaryl derivatives were synthesized by Suzuki–Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that th...

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Main Authors:	Phil M. Pithan, David Decker, Manlio Sutero Sardo, Giampietro Viola, Heiko Ihmels
Format:	Article
Language:	English
Published:	Beilstein-Institut 2016-05-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	fluorescence heterocycles quinolizinium solvatochromism
Online Access:	https://doi.org/10.3762/bjoc.12.84

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spelling	doaj-6840f52159974753a267e8bab020cde72021-02-02T00:48:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-05-0112185486210.3762/bjoc.12.841860-5397-12-84Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivativesPhil M. Pithan0David Decker1Manlio Sutero Sardo2Giampietro Viola3Heiko Ihmels4Department of Chemistry and Biology, University of Siegen and Center of Micro and Nanochemistry and Engineering, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyDepartment of Chemistry and Biology, University of Siegen and Center of Micro and Nanochemistry and Engineering, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyUniversity of Padova, Department of Pharmaceutical and Pharmacological Sciences, via Marzolo 5, 35131 Padova, ItalyUniversity of Padova, Department of Woman’s and Child’s health, 35128 Padova, ItalyDepartment of Chemistry and Biology, University of Siegen and Center of Micro and Nanochemistry and Engineering, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyCationic biaryl derivatives were synthesized by Suzuki–Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with increasing solvent polarity. This red-shifted emission in polar solvents is explained by a charge shift (CS) in the excited state and subsequent solvent relaxation. Furthermore, the polarity of protic polar and aprotic polar solvents affects the emission energy to different extent, which indicates a major influence of hydrogen bonding on the stabilization of the ground and excited states.https://doi.org/10.3762/bjoc.12.84fluorescenceheterocyclesquinoliziniumsolvatochromism
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Phil M. Pithan David Decker Manlio Sutero Sardo Giampietro Viola Heiko Ihmels
spellingShingle	Phil M. Pithan David Decker Manlio Sutero Sardo Giampietro Viola Heiko Ihmels Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives Beilstein Journal of Organic Chemistry fluorescence heterocycles quinolizinium solvatochromism
author_facet	Phil M. Pithan David Decker Manlio Sutero Sardo Giampietro Viola Heiko Ihmels
author_sort	Phil M. Pithan
title	Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
title_short	Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
title_full	Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
title_fullStr	Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
title_full_unstemmed	Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
title_sort	synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2016-05-01
description	Cationic biaryl derivatives were synthesized by Suzuki–Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with increasing solvent polarity. This red-shifted emission in polar solvents is explained by a charge shift (CS) in the excited state and subsequent solvent relaxation. Furthermore, the polarity of protic polar and aprotic polar solvents affects the emission energy to different extent, which indicates a major influence of hydrogen bonding on the stabilization of the ground and excited states.
topic	fluorescence heterocycles quinolizinium solvatochromism
url	https://doi.org/10.3762/bjoc.12.84
work_keys_str_mv	AT philmpithan synthesisandfluorosolvatochromismof3arylnaphtho12bquinoliziniumderivatives AT daviddecker synthesisandfluorosolvatochromismof3arylnaphtho12bquinoliziniumderivatives AT manliosuterosardo synthesisandfluorosolvatochromismof3arylnaphtho12bquinoliziniumderivatives AT giampietroviola synthesisandfluorosolvatochromismof3arylnaphtho12bquinoliziniumderivatives AT heikoihmels synthesisandfluorosolvatochromismof3arylnaphtho12bquinoliziniumderivatives
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Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

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