N-Annulated perylene-substituted and fused porphyrin dimers with intense near-infrared one-photon and two-photon absorption
Type
ArticleAuthors
Luo, JieLee, Sangsu
Son, Minjung
Zheng, Bin

Huang, Kuo-Wei

Qi, Qingbiao
Zeng, Wangdong
Li, Gongqiang
Kim, Dongho
Wu, Jishan
KAUST Department
Chemical Science ProgramHomogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2015-01-21Online Publication Date
2015-01-21Print Publication Date
2015-02-23Permanent link to this record
http://hdl.handle.net/10754/564017
Metadata
Show full item recordAbstract
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.Citation
Luo, J., Lee, S., Son, M., Zheng, B., Huang, K.-W., Qi, Q., … Wu, J. (2015). N-Annulated Perylene-Substituted and Fused Porphyrin Dimers with Intense Near-Infrared One-Photon and Two-Photon Absorption. Chemistry - A European Journal, 21(9), 3708–3715. doi:10.1002/chem.201405574Sponsors
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.Publisher
WileyJournal
Chemistry - A European Journalae974a485f413a2113503eed53cd6c53
10.1002/chem.201405574