TY - JOUR
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
N1 - 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.
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>1.3×105M-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.
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>1.3×105M-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.
UR - http://hdl.handle.net/10754/564017
UR - http://doi.wiley.com/10.1002/chem.201405574
UR - http://www.scopus.com/inward/record.url?scp=84921480886&partnerID=8YFLogxK
U2 - 10.1002/chem.201405574
DO - 10.1002/chem.201405574
M3 - Article
SN - 0947-6539
VL - 21
SP - 3708
EP - 3715
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 9
ER -