Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies

Efficient monosubstitution of the non-iodinated, mono-iodinated and di-iodinated m-carborane cluster at one Ccluster has led to the preparation of three single organic molecule-carborane dyads (4–6), which exhibited exceptional fluorescence properties with quantum yield values of 100% in solution, f...

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Authors: Chaari, Mahdi, Kelemen, Zsolt, Choquesillo-Lazarte, Duane, Gaztelumendi, Nerea, Teixidor, Francesc, Viñas, Clara, Nogués, Carme, Núñez Aguilera, Rosario
Format: article
Status:Published version
Publication Date:2019
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/197954
Online Access:http://hdl.handle.net/10261/197954
Access Level:Open access
Keyword:Aggregation-induced emission
Solid-state emission
Charge-transfer
Excimer formation
Boron clusters
O-carboranes
Photoluminescence
Flourescence
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network_name_str España
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dc.title.none.fl_str_mv Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
title Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
spellingShingle Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
Chaari, Mahdi
Aggregation-induced emission
Solid-state emission
Charge-transfer
Excimer formation
Boron clusters
O-carboranes
Photoluminescence
Flourescence
title_short Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
title_full Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
title_fullStr Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
title_full_unstemmed Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
title_sort Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studies
dc.creator.none.fl_str_mv Chaari, Mahdi
Kelemen, Zsolt
Choquesillo-Lazarte, Duane
Gaztelumendi, Nerea
Teixidor, Francesc
Viñas, Clara
Nogués, Carme
Núñez Aguilera, Rosario
author Chaari, Mahdi
author_facet Chaari, Mahdi
Kelemen, Zsolt
Choquesillo-Lazarte, Duane
Gaztelumendi, Nerea
Teixidor, Francesc
Viñas, Clara
Nogués, Carme
Núñez Aguilera, Rosario
author_role author
author2 Kelemen, Zsolt
Choquesillo-Lazarte, Duane
Gaztelumendi, Nerea
Teixidor, Francesc
Viñas, Clara
Nogués, Carme
Núñez Aguilera, Rosario
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Generalitat de Catalunya
European Commission
Ministerio de Ciencia, Innovación y Universidades (España)
Consejo Superior de Investigaciones Científicas (España)
Chaari, Mahdi [0000-0002-1888-2545]
Kelemen, Zsolt [0000-0002-4787-9804]
Gaztelumendi, Nerea [0000-0002-3837-2956]
Teixidor, Francesc [0000-0002-3010-2417]
Viñas, Clara [0000-0001-5000-0277]
Nogués, Carme [0000-0002-6361-8559]
Núñez Aguilera, Rosario [0000-0003-4582-5148]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Aggregation-induced emission
Solid-state emission
Charge-transfer
Excimer formation
Boron clusters
O-carboranes
Photoluminescence
Flourescence
topic Aggregation-induced emission
Solid-state emission
Charge-transfer
Excimer formation
Boron clusters
O-carboranes
Photoluminescence
Flourescence
description Efficient monosubstitution of the non-iodinated, mono-iodinated and di-iodinated m-carborane cluster at one Ccluster has led to the preparation of three single organic molecule-carborane dyads (4–6), which exhibited exceptional fluorescence properties with quantum yield values of 100% in solution, for all of them, with maxima around 415 nm, which correspond to the locally excited state (LE) emission. These results suggest that simply linking the m-carborane fragment to one anthracene unit through a CH2 spacer produces a significant enhancement of the fluorescence in the final fluorophore, probably due to the free rotation of the anthracene linked to the Ccluster. Besides, the presence of one or two iodine atoms linked to boron atoms does not cause any influence on the photophysical properties of the dyads, as it is confirmed by TD-DFT calculations. Notably, the three conjugates show good fluorescence efficiency in the aggregate state with quantum yields in the range of 19–23%, which could be ascribed to the presence of CH2, particularly for 4, and the iodine atoms in 5 and 6, which prevent π–π stacking. All these results indicate that our dyads are extremely good emitters in solution while maintaining the emission properties in the aggregate state. Crystal packing, fingerprint plot analysis, and TD-DFT calculations for the three compounds support these results. Confocal microscopy studies show that 6 is the best-internalized compound by HeLa cells via endocytosis, although 4 and 5 also presented a high fluorescence intensity emission. Moreover, due to the blue emission, this compound is an excellent candidate to be applied as a fluorescent dye in bioimaging studies.
publishDate 2019
dc.date.none.fl_str_mv 2019
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/197954
url http://hdl.handle.net/10261/197954
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
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dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
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spelling Efficient blue light emitting materials based on m-carborane–anthracene dyads. Structure, photophysics and bioimaging studiesChaari, MahdiKelemen, ZsoltChoquesillo-Lazarte, DuaneGaztelumendi, NereaTeixidor, FrancescViñas, ClaraNogués, CarmeNúñez Aguilera, RosarioAggregation-induced emissionSolid-state emissionCharge-transferExcimer formationBoron clustersO-carboranesPhotoluminescenceFlourescenceEfficient monosubstitution of the non-iodinated, mono-iodinated and di-iodinated m-carborane cluster at one Ccluster has led to the preparation of three single organic molecule-carborane dyads (4–6), which exhibited exceptional fluorescence properties with quantum yield values of 100% in solution, for all of them, with maxima around 415 nm, which correspond to the locally excited state (LE) emission. These results suggest that simply linking the m-carborane fragment to one anthracene unit through a CH2 spacer produces a significant enhancement of the fluorescence in the final fluorophore, probably due to the free rotation of the anthracene linked to the Ccluster. Besides, the presence of one or two iodine atoms linked to boron atoms does not cause any influence on the photophysical properties of the dyads, as it is confirmed by TD-DFT calculations. Notably, the three conjugates show good fluorescence efficiency in the aggregate state with quantum yields in the range of 19–23%, which could be ascribed to the presence of CH2, particularly for 4, and the iodine atoms in 5 and 6, which prevent π–π stacking. All these results indicate that our dyads are extremely good emitters in solution while maintaining the emission properties in the aggregate state. Crystal packing, fingerprint plot analysis, and TD-DFT calculations for the three compounds support these results. Confocal microscopy studies show that 6 is the best-internalized compound by HeLa cells via endocytosis, although 4 and 5 also presented a high fluorescence intensity emission. Moreover, due to the blue emission, this compound is an excellent candidate to be applied as a fluorescent dye in bioimaging studies.The work was supported by the Spanish Ministerio de Economía y Competitividad, MINECO (CTQ2016-75150-R, MAT2017-86357-C3-3-R and “Severo Ochoa” Program for Centers of Excellence in R&D SEV-2015-0496) and Generalitat de Catalunya (2017/SGR/1720, 2017/SGR/503). Z. K. is grateful for the general support of the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement MSCA-IF-2016-751587. D. Ch.-L. acknowledges funding from the Intramural CSIC (201730I019) project. Theoretical calculations have been achieved using computers from the Supercomputing Centre of Catalonia (CESCA). The authors would like to thank the staff at the Servei de Microscòpia de la Universitat Autònoma de Barcelona.We acknowledge support by the CSIC Open Access Publication Initiative through its Unit of Information Resources for Research (URICI).Peer reviewedRoyal Society of Chemistry (UK)Ministerio de Economía y Competitividad (España)Generalitat de CatalunyaEuropean CommissionMinisterio de Ciencia, Innovación y Universidades (España)Consejo Superior de Investigaciones Científicas (España)Chaari, Mahdi [0000-0002-1888-2545]Kelemen, Zsolt [0000-0002-4787-9804]Gaztelumendi, Nerea [0000-0002-3837-2956]Teixidor, Francesc [0000-0002-3010-2417]Viñas, Clara [0000-0001-5000-0277]Nogués, Carme [0000-0002-6361-8559]Núñez Aguilera, Rosario [0000-0003-4582-5148]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/197954reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75150-RMICIU/ICTI2017-2020/MAT2017-86357-C3-3-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SEV-2015-0496info:eu-repo/grantAgreement/EC/H2020/751587http://dx.doi.org/10.1039/C9BM00903ESíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1979542026-05-22T06:33:51Z
score 15.812429

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