Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates

Abstract All-organic thermally activated delayed fluorescence (TADF) materials have emerged as potential candidates for optoelectronic devices and biomedical applications. However, the development of organic TADF probes with strong emission in the longer wavelength region (> 600 nm) rem...

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Autores principales: Subhadeep Das, Subhankar Kundu, Bahadur Sk, Madhurima Sarkar, Abhijit Patra
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Lenguaje:EN
Publicado: Georg Thieme Verlag 2021
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spelling oai:doaj.org-article:c18945767b014e4ea2bd068def0d1fdd2021-11-27T00:45:19ZRed Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates2625-182510.1055/a-1679-9558https://doaj.org/article/c18945767b014e4ea2bd068def0d1fdd2021-10-01T00:00:00Zhttp://www.thieme-connect.de/DOI/DOI?10.1055/a-1679-9558https://doaj.org/toc/2625-1825Abstract All-organic thermally activated delayed fluorescence (TADF) materials have emerged as potential candidates for optoelectronic devices and biomedical applications. However, the development of organic TADF probes with strong emission in the longer wavelength region (> 600 nm) remains a challenge. Strong π-conjugated rigid acceptor cores substituted with multiple donor units can be a viable design strategy to obtain red TADF probes. Herein, 3,6-di-t-butyl carbazole substituted to a dibenzopyridoquinoxaline acceptor core resulted in a T-shaped donor–acceptor–donor compound, PQACz-T, exhibiting red TADF in polymer-embedded thin-films. Further, PQACz-T self-assembled to molecular nanoaggregates of diverse size and shape in THF–water mixture showing bright red emission along with delayed fluorescence even in an aqueous environment. The self-assembly and the excited-state properties of PQACz-T were compared with the nonalkylated analogue, PQCz-T. The delayed fluorescence in nanoaggregates was attributed to the high rate of reverse intersystem crossing. Moreover, an aqueous dispersion of the smaller-sized, homogeneous distribution of fluorescent nanoparticles was fabricated upon encapsulating PQACz-T in a triblock copolymer, F-127. Cytocompatible polymer-encapsulated PQACz-T nanoparticles with large Stokes shift and excellent photostability were demonstrated for the specific imaging of lipid droplets in HeLa cells.Subhadeep DasSubhankar KunduBahadur SkMadhurima SarkarAbhijit PatraGeorg Thieme Verlagarticletadfdibenzopyridoquinoxalinenanoaggregatesfluorescence imaginglipid dropletsChemistryQD1-999ENOrganic Materials, Vol 3, Iss 04, Pp 477-487 (2021)
institution DOAJ
collection DOAJ
language EN
topic tadf
dibenzopyridoquinoxaline
nanoaggregates
fluorescence imaging
lipid droplets
Chemistry
QD1-999
spellingShingle tadf
dibenzopyridoquinoxaline
nanoaggregates
fluorescence imaging
lipid droplets
Chemistry
QD1-999
Subhadeep Das
Subhankar Kundu
Bahadur Sk
Madhurima Sarkar
Abhijit Patra
Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
description Abstract All-organic thermally activated delayed fluorescence (TADF) materials have emerged as potential candidates for optoelectronic devices and biomedical applications. However, the development of organic TADF probes with strong emission in the longer wavelength region (> 600 nm) remains a challenge. Strong π-conjugated rigid acceptor cores substituted with multiple donor units can be a viable design strategy to obtain red TADF probes. Herein, 3,6-di-t-butyl carbazole substituted to a dibenzopyridoquinoxaline acceptor core resulted in a T-shaped donor–acceptor–donor compound, PQACz-T, exhibiting red TADF in polymer-embedded thin-films. Further, PQACz-T self-assembled to molecular nanoaggregates of diverse size and shape in THF–water mixture showing bright red emission along with delayed fluorescence even in an aqueous environment. The self-assembly and the excited-state properties of PQACz-T were compared with the nonalkylated analogue, PQCz-T. The delayed fluorescence in nanoaggregates was attributed to the high rate of reverse intersystem crossing. Moreover, an aqueous dispersion of the smaller-sized, homogeneous distribution of fluorescent nanoparticles was fabricated upon encapsulating PQACz-T in a triblock copolymer, F-127. Cytocompatible polymer-encapsulated PQACz-T nanoparticles with large Stokes shift and excellent photostability were demonstrated for the specific imaging of lipid droplets in HeLa cells.
format article
author Subhadeep Das
Subhankar Kundu
Bahadur Sk
Madhurima Sarkar
Abhijit Patra
author_facet Subhadeep Das
Subhankar Kundu
Bahadur Sk
Madhurima Sarkar
Abhijit Patra
author_sort Subhadeep Das
title Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
title_short Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
title_full Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
title_fullStr Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
title_full_unstemmed Red Thermally Activated Delayed Fluorescence in Dibenzopyridoquinoxaline-Based Nanoaggregates
title_sort red thermally activated delayed fluorescence in dibenzopyridoquinoxaline-based nanoaggregates
publisher Georg Thieme Verlag
publishDate 2021
url https://doaj.org/article/c18945767b014e4ea2bd068def0d1fdd
work_keys_str_mv AT subhadeepdas redthermallyactivateddelayedfluorescenceindibenzopyridoquinoxalinebasednanoaggregates
AT subhankarkundu redthermallyactivateddelayedfluorescenceindibenzopyridoquinoxalinebasednanoaggregates
AT bahadursk redthermallyactivateddelayedfluorescenceindibenzopyridoquinoxalinebasednanoaggregates
AT madhurimasarkar redthermallyactivateddelayedfluorescenceindibenzopyridoquinoxalinebasednanoaggregates
AT abhijitpatra redthermallyactivateddelayedfluorescenceindibenzopyridoquinoxalinebasednanoaggregates
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