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Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources

Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low‐intensity ECD spectr...

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Autores principales: Zullo, Valerio, Iuliano, Anna, Pescitelli, Gennaro, Zinna, Francesco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303411/
https://www.ncbi.nlm.nih.gov/pubmed/34982485
http://dx.doi.org/10.1002/chem.202104226
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author Zullo, Valerio
Iuliano, Anna
Pescitelli, Gennaro
Zinna, Francesco
author_facet Zullo, Valerio
Iuliano, Anna
Pescitelli, Gennaro
Zinna, Francesco
author_sort Zullo, Valerio
collection PubMed
description Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low‐intensity ECD spectra were obtained, suggesting the absence of chromophore interaction in the ground state, except in the case of isomannide bis‐perylenecarboxylate, whose ECD spectrum showed a positive exciton couplet. All isomannide derivatives, with the only exception of the one containing a pyrenecarboxylate and a perylenecarboxylate, exhibited excimer CPL spectra, whereas isosorbide derivatives did not show any CPL. Isomannide derivatives bearing two pyrenecarboxylate or two pyrenylacetate groups showed positive CPL emission with dissymmetry factors up to 10(−2), which depends on the conformational freedom of the appended units. The CPL sign, Stokes shift and order of magnitude of dissymmetry factor were reproduced by excited‐state calculations on a representative compound. Interestingly, the mixed derivative containing pyrenic units with different spacing from the isomannide scaffold showed an oppositely signed excimer band with respect to the homo‐substituted derivatives.
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spelling pubmed-93034112022-07-22 Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources Zullo, Valerio Iuliano, Anna Pescitelli, Gennaro Zinna, Francesco Chemistry Research Articles Organic compounds showing circularly polarized luminescence (CPL) are at the forefront of novel applications and technologies. Here we show the synthesis and chiroptical properties of pyrene and perylene derivatives of inexpensive chiral scaffolds: isomannide and isosorbide. Low‐intensity ECD spectra were obtained, suggesting the absence of chromophore interaction in the ground state, except in the case of isomannide bis‐perylenecarboxylate, whose ECD spectrum showed a positive exciton couplet. All isomannide derivatives, with the only exception of the one containing a pyrenecarboxylate and a perylenecarboxylate, exhibited excimer CPL spectra, whereas isosorbide derivatives did not show any CPL. Isomannide derivatives bearing two pyrenecarboxylate or two pyrenylacetate groups showed positive CPL emission with dissymmetry factors up to 10(−2), which depends on the conformational freedom of the appended units. The CPL sign, Stokes shift and order of magnitude of dissymmetry factor were reproduced by excited‐state calculations on a representative compound. Interestingly, the mixed derivative containing pyrenic units with different spacing from the isomannide scaffold showed an oppositely signed excimer band with respect to the homo‐substituted derivatives. John Wiley and Sons Inc. 2022-02-15 2022-03-10 /pmc/articles/PMC9303411/ /pubmed/34982485 http://dx.doi.org/10.1002/chem.202104226 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Zullo, Valerio
Iuliano, Anna
Pescitelli, Gennaro
Zinna, Francesco
Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title_full Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title_fullStr Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title_full_unstemmed Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title_short Tunable Excimer Circularly Polarized Luminescence in Isohexide Derivatives from Renewable Resources
title_sort tunable excimer circularly polarized luminescence in isohexide derivatives from renewable resources
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303411/
https://www.ncbi.nlm.nih.gov/pubmed/34982485
http://dx.doi.org/10.1002/chem.202104226
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