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

Jie Luo, Sangsu Lee, Minjung Son, Bin Zheng, Kuo Wei Huang, Qingbiao Qi, Wangdong Zeng, Gongqiang Li, Dongho Kim, Jishan Wu

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 × 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 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.

Original languageEnglish
Pages (from-to)3708-3715
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number9
DOIs
Publication statusPublished - 2015 Jan 21

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Perylene
Porphyrins
Dimers
Photons
Infrared radiation
Chromophores
Fluorescence
Quantum yield
Excited states
Electronic structure
Density functional theory
Absorption spectra
Coloring Agents
Fusion reactions
Dyes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Luo, Jie ; Lee, Sangsu ; Son, Minjung ; Zheng, Bin ; Huang, Kuo Wei ; Qi, Qingbiao ; Zeng, Wangdong ; Li, Gongqiang ; Kim, Dongho ; Wu, Jishan. / N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 9. pp. 3708-3715.
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N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption. / Luo, Jie; Lee, Sangsu; Son, Minjung; Zheng, Bin; Huang, Kuo Wei; Qi, Qingbiao; Zeng, Wangdong; Li, Gongqiang; Kim, Dongho; Wu, Jishan.

In: Chemistry - A European Journal, Vol. 21, No. 9, 21.01.2015, p. 3708-3715.

Research output: Contribution to journalArticle

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T1 - N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption

AU - Luo, Jie

AU - Lee, Sangsu

AU - Son, Minjung

AU - Zheng, Bin

AU - Huang, Kuo Wei

AU - Qi, Qingbiao

AU - Zeng, Wangdong

AU - Li, Gongqiang

AU - Kim, Dongho

AU - Wu, Jishan

PY - 2015/1/21

Y1 - 2015/1/21

N2 - 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 × 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 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.

AB - 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 × 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 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.

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