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Article: Alkoxy-Substituted Quadrupolar Fluorescent Dyes

TitleAlkoxy-Substituted Quadrupolar Fluorescent Dyes
Authors
Issue Date2022
Citation
Journal of the American Chemical Society, 2022, v. 144, n. 37, p. 16841-16854 How to Cite?
AbstractPolar and polarizable π-conjugated organic molecules containing push-pull chromophores have been investigated extensively in the past. Identifying unique backbones and building blocks for fluorescent dyes is a timely exercise. Here, we report the synthesis and characterization of a series of fluorescent dyes containing quadrupolar A-D-A constitutions (where A = acceptor and D = donor), which exhibit fluorescence emission at a variety of different wavelengths. We have investigated the effects of different electron-withdrawing groups, located at both termini of a para-terphenylene backbone, by steady-state UV/vis and fluorescence spectroscopy. Pyridine and substituted pyridinium units are also introduced during the construction of the quadrupolar backbones. Depending on the quadrupolarity, fluorescence emission wavelengths cover from 380 to 557 nm. Time-resolved absorption and emission spectroscopy reveal that the photophysical properties of those quadrupolar dyes result from intramolecular charge transfer. One of the dyes we have investigated is a symmetrical box-like tetracationic cyclophane. Its water-soluble tetrachloride, which is non-cytotoxic to cells up to a loading concentration of 1 μM, has been employed in live-cell imaging. When taken up by cells, the tetrachloride emits a green fluorescence emission without any hint of photobleaching or disruption of normal cell behavior. We envision that our design strategy of modifying molecules through the functionalization of the quadrupolar building blocks as chromophores will lead to future generations of fluorescent dyes in which these A-D-A constitutional fragments are incorporated into more complex molecules and polymers for broader photophysical and biological applications.
Persistent Identifierhttp://hdl.handle.net/10722/333556
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorFeng, Yuanning-
dc.contributor.authorDas, Partha Jyoti-
dc.contributor.authorYoung, Ryan M.-
dc.contributor.authorBrown, Paige J.-
dc.contributor.authorHornick, Jessica E.-
dc.contributor.authorWeber, Jacob A.-
dc.contributor.authorSeale, James S.W.-
dc.contributor.authorStern, Charlotte L.-
dc.contributor.authorWasielewski, Michael R.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:20:33Z-
dc.date.available2023-10-06T05:20:33Z-
dc.date.issued2022-
dc.identifier.citationJournal of the American Chemical Society, 2022, v. 144, n. 37, p. 16841-16854-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/333556-
dc.description.abstractPolar and polarizable π-conjugated organic molecules containing push-pull chromophores have been investigated extensively in the past. Identifying unique backbones and building blocks for fluorescent dyes is a timely exercise. Here, we report the synthesis and characterization of a series of fluorescent dyes containing quadrupolar A-D-A constitutions (where A = acceptor and D = donor), which exhibit fluorescence emission at a variety of different wavelengths. We have investigated the effects of different electron-withdrawing groups, located at both termini of a para-terphenylene backbone, by steady-state UV/vis and fluorescence spectroscopy. Pyridine and substituted pyridinium units are also introduced during the construction of the quadrupolar backbones. Depending on the quadrupolarity, fluorescence emission wavelengths cover from 380 to 557 nm. Time-resolved absorption and emission spectroscopy reveal that the photophysical properties of those quadrupolar dyes result from intramolecular charge transfer. One of the dyes we have investigated is a symmetrical box-like tetracationic cyclophane. Its water-soluble tetrachloride, which is non-cytotoxic to cells up to a loading concentration of 1 μM, has been employed in live-cell imaging. When taken up by cells, the tetrachloride emits a green fluorescence emission without any hint of photobleaching or disruption of normal cell behavior. We envision that our design strategy of modifying molecules through the functionalization of the quadrupolar building blocks as chromophores will lead to future generations of fluorescent dyes in which these A-D-A constitutional fragments are incorporated into more complex molecules and polymers for broader photophysical and biological applications.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleAlkoxy-Substituted Quadrupolar Fluorescent Dyes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.2c04906-
dc.identifier.pmid36083184-
dc.identifier.scopuseid_2-s2.0-85137858911-
dc.identifier.volume144-
dc.identifier.issue37-
dc.identifier.spage16841-
dc.identifier.epage16854-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000859293700001-

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