The interplay of intersystem crossing and internal conversion in quadrupolar tetraarylpyrrolo[3,2- b]pyrroles

Simple item record

Full item record

dc.contributor.authorGórski, Krzysztof
dc.contributor.authorKusy, Damian
dc.contributor.authorOzaki, Shuhei
dc.contributor.authorBanasiewicz, Marzena
dc.contributor.authorValiev, Rashid
dc.contributor.authorSahoo, Smruti Ranjan
dc.contributor.authorKamada, Kenji
dc.contributor.authorBaryshnikov, Glib
dc.contributor.authorGryko, Daniel Tomasz
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.contributor.organizationNMRI, National Institute of Advanced Industrial Science and Technology (AIST), Japan
dc.contributor.organizationDepartment of Chemistry, Graduate School of Science and Technology, Kwansei Gakuin University, Japan
dc.contributor.organizationInstitute of Physics, Polish Academy of Sciences
dc.contributor.organizationDepartment of Chemistry, University of Helsinki, Finland
dc.contributor.organizationLaboratory of Organic Electronics, Department of Science and Technology, Linköping University, Sweden
dc.contributor.organizationDepartment of Chemistry and Nanomaterials Science, Bohdan Khmelnytsky National University, Ukraine
dc.date.accessioned2024-05-24T14:15:30Z
dc.date.available2024-05-24T14:15:30Z
dc.date.issued2024
dc.description.abstractAdding nitro groups to aromatic compounds usually quenches their fluorescence via intersystem crossing (ISC) or internal conversion (IC). Herein, we investigated centrosymmetric 1,4-dihydropyrrolo[3,2-b]pyrroles linked to variously substituted nitro-heteroaryls. A 1,4-orientation of the nitro substituent versus the electron rich 1,4-dihydropyrrolo[3,2-b]pyrrole core invokes a strong fluorescence in non-polar solvents and intense two-photon absorption while a 1,3-orientation of push–pull substituents results in a dramatic hypsochromic shift of absorption, weak, bathochromically shifted emission and weak two-photon absorption. The combined experimental and computational study indicates that the primary responsible factors are: (1) the difference in electron density distribution in the LUMO; (2) the difference in μ10. IC is a dominant mechanism of non-radiative dissipation of energy in all these dyes but as long as the distribution of electron density within the HOMO and LUMO is delocalized on the 1,4-dihydropyrrolo[3,2-b]pyrrole core as well as on the nitroaromatic moieties its rate is slower than the fluorescence rate in non-polar solvents.en
dc.description.sponsorshipFoundation for Polish Science (TEAM POIR.04.04.00-00-3CF4/16-00); National Science Centre, Poland, under QuantERA programme, project 2017/25/Z/ST2/03038 and OPUS 2020/37/B/ST4/00017; European Union's Horizon 2020 research and innovation programme under the Marie Skłodowka-Curie grant agreement no. 101007804; JSPS KAKENHI Grant Number 21H01887; Ministry of Education and Science of Ukraine for support (Project No. 0121U107533); Academy of Finland through project 346369; National Academic Infrastructure for Supercomputing in Sweden (NAISS 2023/5-77) at the National Supercomputer Centre (NSC) at Linköping University partially funded by the Swedish Research Council through grant agreement no. 2022-06725; Swedish Research Council through starting grant no. 2020-04600; Olle Engkvists Stiftelse (Sweden), project number 212-0136.
dc.identifier.citationJ. Mater. Chem. C, 2024, 12, 1980–1987. https://doi.org/10.1039/D3TC03851C
dc.identifier.doi10.1039/d3tc03851c
dc.identifier.issn2050-7526
dc.identifier.issn2050-7534
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/24326
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.rightsUznanie autorstwa-Użycie niekomercyjne 3.0 Unporteden
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/
dc.sourceJournal of Materials Chemistry C
dc.titleThe interplay of intersystem crossing and internal conversion in quadrupolar tetraarylpyrrolo[3,2- b]pyrrolesen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidGórski, Krzysztof [0000-0002-6439-2651]
person.identifier.orcidKusy, Damian [0000-0002-0643-3478]
person.identifier.orcidGryko, Daniel Tomasz [0000-0002-2146-1282]
Files for this record
Original bundle
Now showing 1 - 1 of 1
Name: d3tc03851c.pdf
Size: 1.26 MB
Format: Adobe Portable Document Format
Description:
Download
License files
Name: license_rdf
Size: 1 KB
Format: RDF serialized in XML
Description:
Download
Belongs to collection
Artykuły IChO PAN