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 journalArticlepeer-review

18 Scopus citations


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.
Original languageEnglish (US)
Pages (from-to)3708-3715
Number of pages8
JournalChemistry - A European Journal
Issue number9
StatePublished - Jan 21 2015

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

ASJC Scopus subject areas

  • Chemistry(all)


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