A new auspicious scaffold for small dyes and fluorophores
An unprecedented chromophore, based on a nitrogen fused tricyclic heterocycle, is presented. This prototype molecule can be considered a “rigidified” monomethine cyanine dye and the central core is isoelectronic to pyridine-based BODIPY analogues, such as boron difluoride dipyridylmethene. The chrom...
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| Published in: | Dyes and pigments Vol. 197; p. 109849 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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01.01.2022
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| ISSN: | 0143-7208, 1873-3743 |
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| Abstract | An unprecedented chromophore, based on a nitrogen fused tricyclic heterocycle, is presented. This prototype molecule can be considered a “rigidified” monomethine cyanine dye and the central core is isoelectronic to pyridine-based BODIPY analogues, such as boron difluoride dipyridylmethene. The chromophore was synthesized and its photophysical properties examined. The new molecule can be considered the starting point to develop dyes, fluorophores or dual-emission fluorescent probes with excitation window in the green region of the spectrum. |
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| AbstractList | An unprecedented chromophore, based on a nitrogen fused tricyclic heterocycle, is presented. This prototype molecule can be considered a “rigidified” monomethine cyanine dye and the central core is isoelectronic to pyridine-based BODIPY analogues, such as boron difluoride dipyridylmethene. The chromophore was synthesized and its photophysical properties examined. The new molecule can be considered the starting point to develop dyes, fluorophores or dual-emission fluorescent probes with excitation window in the green region of the spectrum. |
| ArticleNumber | 109849 |
| Author | Volpi, Giorgio Priola, Emanuele Barolo, Claudia Garino, Claudio |
| Author_xml | – sequence: 1 givenname: Giorgio orcidid: 0000-0002-9695-9202 surname: Volpi fullname: Volpi, Giorgio organization: Dept. of Chemistry and NIS Interdepartmental Centre, University of Turin, Italy – sequence: 2 givenname: Claudio orcidid: 0000-0002-7854-6076 surname: Garino fullname: Garino, Claudio email: claudio.garino@unito.it organization: Dept. of Chemistry and NIS Interdepartmental Centre, University of Turin, Italy – sequence: 3 givenname: Emanuele orcidid: 0000-0002-0270-738X surname: Priola fullname: Priola, Emanuele organization: Dept. of Chemistry and NIS Interdepartmental Centre, University of Turin, Italy – sequence: 4 givenname: Claudia surname: Barolo fullname: Barolo, Claudia organization: Dept. of Chemistry and NIS Interdepartmental Centre, University of Turin, Italy |
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| Cites_doi | 10.1016/j.cbpa.2011.10.013 10.1002/chem.201502921 10.1002/ange.19610732206 10.1021/acsami.6b08338 10.1039/C5CC09345G 10.1002/cber.19620950610 10.1016/j.dyepig.2017.04.034 10.1039/C4AN01172D 10.1146/annurev-physiol-022516-034055 10.1039/C9RA10290F 10.1039/c1cc00078k 10.1021/cb1002416 10.1021/acs.joc.7b00786 10.1039/C4CS00365A 10.1002/anie.200702070 10.1007/s00424-013-1234-z 10.1002/ejoc.201000343 10.1055/s-0035-1561489 10.1021/acs.iecr.9b01906 10.1021/cb4000822 10.1016/S1386-1425(01)00476-0 10.1016/j.dyepig.2018.04.037 10.1039/C8RA02297F 10.1146/annurev-biochem-061516-044839 10.1021/acs.orglett.7b03291 10.1021/acscentsci.7b00247 10.1021/cb700248m |
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10.1016/j.dyepig.2021.109849_bib8 article-title: Bright ideas for chemical biology publication-title: ACS Chem Biol doi: 10.1021/cb700248m |
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| SubjectTerms | Dual emission fluorescent probe Green light absorber Monomethine cyanine pH sensitive chromophore Small dye Small fluorophore |
| Title | A new auspicious scaffold for small dyes and fluorophores |
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