N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption

Handle URI:
http://hdl.handle.net/10754/564017
Title:
N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption
Authors:
Luo, Jie; Lee, Sangsu; Son, Minjung; Zheng, Bin; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Qi, Qingbiao; Zeng, Wangdong; Li, Gongqiang; Kim, Dongho; Wu, Jishan
Abstract:
Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S0-S1 electronic transition moment axis has resulted in new near-infrared (NIR) dyes 1a/1b with very intense absorption (ε>1.3×105M-1cm-1) beyond 1250nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10-6 and 6.0×10-6 for 1a and 1b, respectively. The NP-substituted porphyrin dimers 2a/2b have also been obtained by controlled oxidative coupling and cyclodehydrogenation, and they showed superimposed absorptions of the fused porphyrin dimer and the NP chromophore. The excited-state dynamics of all of these compounds have been studied by femtosecond transient absorption measurements, which revealed porphyrin dimer-like behaviour. These new chromophores also exhibited good nonlinear optical susceptibility with large two-photon absorption cross-sections in the NIR region due to extended π-conjugation. Time-dependent density functional theory calculations have been performed to aid our understanding of their electronic structures and absorption spectra.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
21-Jan-2015
DOI:
10.1002/chem.201405574
Type:
Article
ISSN:
09476539
Sponsors:
J.W. acknowledges financial support from MOE Tier 2 grants (MOE2011-T2-2-130, MOE2014-T2-1-080) and an A*STAR JCO grant (1431AFG100). The work at Yonsei University was financially supported by the Mid-career Researcher Program (2005-0093839) and Global Research Laboratory (2013K1A1A2A02050183) administered through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (MEST). K.-W.H. is grateful for financial support from KAUST.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLuo, Jieen
dc.contributor.authorLee, Sangsuen
dc.contributor.authorSon, Minjungen
dc.contributor.authorZheng, Binen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorQi, Qingbiaoen
dc.contributor.authorZeng, Wangdongen
dc.contributor.authorLi, Gongqiangen
dc.contributor.authorKim, Donghoen
dc.contributor.authorWu, Jishanen
dc.date.accessioned2015-08-03T12:28:36Zen
dc.date.available2015-08-03T12:28:36Zen
dc.date.issued2015-01-21en
dc.identifier.issn09476539en
dc.identifier.doi10.1002/chem.201405574en
dc.identifier.urihttp://hdl.handle.net/10754/564017en
dc.description.abstractFusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S0-S1 electronic transition moment axis has resulted in new near-infrared (NIR) dyes 1a/1b with very intense absorption (ε>1.3×105M-1cm-1) beyond 1250nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10-6 and 6.0×10-6 for 1a and 1b, respectively. The NP-substituted porphyrin dimers 2a/2b have also been obtained by controlled oxidative coupling and cyclodehydrogenation, and they showed superimposed absorptions of the fused porphyrin dimer and the NP chromophore. The excited-state dynamics of all of these compounds have been studied by femtosecond transient absorption measurements, which revealed porphyrin dimer-like behaviour. These new chromophores also exhibited good nonlinear optical susceptibility with large two-photon absorption cross-sections in the NIR region due to extended π-conjugation. Time-dependent density functional theory calculations have been performed to aid our understanding of their electronic structures and absorption spectra.en
dc.description.sponsorshipJ.W. acknowledges financial support from MOE Tier 2 grants (MOE2011-T2-2-130, MOE2014-T2-1-080) and an A*STAR JCO grant (1431AFG100). The work at Yonsei University was financially supported by the Mid-career Researcher Program (2005-0093839) and Global Research Laboratory (2013K1A1A2A02050183) administered through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (MEST). K.-W.H. is grateful for financial support from KAUST.en
dc.publisherWiley-Blackwellen
dc.subjectNear-infrared dyeen
dc.subjectNonlinear opticsen
dc.subjectPorphyrinoidsen
dc.subjectRyleneen
dc.subjectTransient absorptionen
dc.subjectTwo-photon absorptionen
dc.titleN-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorptionen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionInstitute of Materials Research and Engineering (IMRE), ASTAR (Agency for Science, Technology and Research), 3 Research LinkSingapore, Singaporeen
dc.contributor.institutionDepartment of Chemistry, Yonsei UniversitySeoul, South Koreaen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3Singapore, Singaporeen
kaust.authorZheng, Binen
kaust.authorHuang, Kuo-Weien
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