N-Annulated Perylene-Substituted and Fused Porphyrin Dimers with Intense Near-Infrared One-Photon and Two-Photon Absorption

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 1 a/1 b with very intense absorption (ε>1.3×105 M−1 cm−1) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence wi...

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Published inChemistry : a European journal Vol. 21; no. 9; pp. 3708 - 3715
Main Authors Luo, Jie, Lee, Sangsu, Son, Minjung, Zheng, Bin, Huang, Kuo-Wei, Qi, Qingbiao, Zeng, Wangdong, Li, Gongqiang, Kim, Dongho, Wu, Jishan
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 23.02.2015
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Absorption
Chemistry
Chemistry, Multidisciplinary
Chromophores
Cross sections
Dimers
Dyes
Electronics
Fluorescence
near-infrared dye
Nonlinear dynamics
nonlinear optics
Physical Sciences
porphyrinoids
Porphyrins
rylene
Science & Technology
transient absorption
two-photon absorption
CRYSTAL-STRUCTURE
EXPANDED PORPHYRINS
IR ABSORPTION
PHOTOPHYSICAL PROPERTIES
near-infrared dye
transient absorption
BETA
TAPES
nonlinear optics
porphyrinoids
rylene
MESO-MESO
OPTICAL NONLINEARITY
ENHANCEMENT
POLYMER
two-photon absorption
Online AccessGet full text
ISSN0947-6539
1521-3765
1521-3765
DOI10.1002/chem.201405574

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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 1 a/1 b with very intense absorption (ε>1.3×105 M−1 cm−1) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10−6 and 6.0×10−6 for 1 a and 1 b, respectively. The NP‐substituted porphyrin dimers 2 a/2 b 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. Fusion along an axis: Fusion of two N‐annulated perylene units to a fused Zn–porphyrin dimer along the S0–S1 electronic transition moment axis of both has resulted in organic near‐infrared dyes with very intense absorption beyond 1250 nm. They also show large two‐photon absorption cross‐sections.
AbstractList Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S-0-S-1 electronic transition moment axis has resulted in new near-infrared (NIR) dyes 1a/1b with very intense absorption (epsilon>1.3x10(5)M(-1)cm(-1)) beyond 1250nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4x10(-6) and 6.0x10(-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 -conjugation. Time-dependent density functional theory calculations have been performed to aid our understanding of their electronic structures and absorption spectra.
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 1 a/1 b with very intense absorption (ε>1.3×105 M−1 cm−1) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10−6 and 6.0×10−6 for 1 a and 1 b, respectively. The NP‐substituted porphyrin dimers 2 a/2 b 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. Fusion along an axis: Fusion of two N‐annulated perylene units to a fused Zn–porphyrin dimer along the S0–S1 electronic transition moment axis of both has resulted in organic near‐infrared dyes with very intense absorption beyond 1250 nm. They also show large two‐photon absorption cross‐sections.
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 ([epsi]>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.
Fusion of two N ‐annulated perylene (NP) units with a fused porphyrin dimer along the S 0 –S 1 electronic transition moment axis has resulted in new near‐infrared (NIR) dyes 1 a / 1 b with very intense absorption (ε>1.3×10 5   M −1  cm −1 ) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10 −6 and 6.0×10 −6 for 1 a and 1 b , respectively. The NP‐substituted porphyrin dimers 2 a / 2 b 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.
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 1 a/1 b with very intense absorption (ε>1.3×10(5) M(-1) cm(-1)) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10(-6) and 6.0×10(-6) for 1 a and 1 b, respectively. The NP-substituted porphyrin dimers 2 a/2 b 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.
Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S sub(0)-S sub(1) electronic transition moment axis has resulted in new near-infrared (NIR) dyes 1a/1b with very intense absorption ( epsilon >1.310 super(5)M super(-1)cm super(-1)) beyond 1250nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.410 super(-6) and 6.010 super(-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 pi -conjugation. Time-dependent density functional theory calculations have been performed to aid our understanding of their electronic structures and absorption spectra. Fusion along an axis: Fusion of two N-annulated perylene units to a fused Zn-porphyrin dimer along the S sub(0)-S sub(1) electronic transition moment axis of both has resulted in organic near-infrared dyes with very intense absorption beyond 1250nm. They also show large two-photon absorption cross-sections.
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 1 a/1 b with very intense absorption (ε>1.3×10(5) M(-1) cm(-1)) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10(-6) and 6.0×10(-6) for 1 a and 1 b, respectively. The NP-substituted porphyrin dimers 2 a/2 b 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.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 1 a/1 b with very intense absorption (ε>1.3×10(5) M(-1) cm(-1)) beyond 1250 nm. Both compounds displayed moderate NIR fluorescence with fluorescence quantum yields of 4.4×10(-6) and 6.0×10(-6) for 1 a and 1 b, respectively. The NP-substituted porphyrin dimers 2 a/2 b 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.
Author Zheng, Bin
Luo, Jie
Son, Minjung
Li, Gongqiang
Wu, Jishan
Kim, Dongho
Huang, Kuo-Wei
Zeng, Wangdong
Qi, Qingbiao
Lee, Sangsu
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/25606849$$D View this record in MEDLINE/PubMed
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IsScholarly true
Issue 9
Keywords CRYSTAL-STRUCTURE
EXPANDED PORPHYRINS
IR ABSORPTION
PHOTOPHYSICAL PROPERTIES
near-infrared dye
transient absorption
BETA
TAPES
nonlinear optics
porphyrinoids
rylene
MESO-MESO
OPTICAL NONLINEARITY
ENHANCEMENT
POLYMER
two-photon absorption
Language English
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2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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MOE - No. MOE2011-T2-2-130; No. MOE2014-T2-1-080
Ministry of Education, Science and Technology (MEST)
KAUST
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PublicationDate February 23, 2015
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PublicationSubtitle A European Journal
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2014; 16
2005; 109
2014; 18
2008; 112
2003; 125
2006; 128
2007; 19
2007; 129
2004 2004; 43 116
2009; 21
2011
2013; 42
2009
2008; 14
2007
2006; 110
2005
2008; 10
2010 2010; 49 122
2009; 130
2003
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2006 2006; 45 118
1995 1995; 34 107
2002; 124
2005; 127
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References_xml – reference: K. S. Kim, J. M. Lim, A. Osuka, D. Kim, J. Photochem. Photobiol. C. 2008, 9, 13-28;
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– reference: H. Rath, J. Sankar, V. PrabhuRaja, T. K. Chandrashekar, A. Nag, D. Goswami, J. Am. Chem. Soc. 2005, 127, 11608-11609;
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SSID ssj0009633
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Snippet 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...
Fusion of two N ‐annulated perylene (NP) units with a fused porphyrin dimer along the S 0 –S 1 electronic transition moment axis has resulted in new...
Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S-0-S-1 electronic transition moment axis has resulted in new...
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...
Fusion of two N-annulated perylene (NP) units with a fused porphyrin dimer along the S sub(0)-S sub(1) electronic transition moment axis has resulted in new...
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SubjectTerms Absorption
Chemistry
Chemistry, Multidisciplinary
Chromophores
Cross sections
Dimers
Dyes
Electronics
Fluorescence
near-infrared dye
Nonlinear dynamics
nonlinear optics
Physical Sciences
porphyrinoids
Porphyrins
rylene
Science & Technology
transient absorption
two-photon absorption
Title N-Annulated Perylene-Substituted and Fused Porphyrin Dimers with Intense Near-Infrared One-Photon and Two-Photon Absorption
URI https://api.istex.fr/ark:/67375/WNG-05KCRT25-4/fulltext.pdf
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https://www.ncbi.nlm.nih.gov/pubmed/25606849
https://www.proquest.com/docview/1655293476
https://www.proquest.com/docview/1657326101
https://www.proquest.com/docview/1786165203
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