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Charge separation, charge recombination and intersystem crossing in orthogonal naphthalimide–perylene electron donor/acceptor dyad

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Abstract

We prepared an orthogonal electron donor/acceptor dyad (NI–Py) with perylene (Py) as electron donor and 4-aminonaphthalimide (NI) as an electron acceptor. The molecule adopts orthogonal geometry due to the steric hindrance exerted by the 4-amino substituents on the NI moiety. The photophysical properties of dyad were studied by steady-state UV–Vis absorption and fluorescence spectroscopies, femtosecond/nanosecond transient absorption spectroscopies and DFT computations. Ground state interaction between the NI and Py units is negligible; however, charge separation occurs upon photoexcitation, indicated by the quenching of the fluorescence of the dyad in polar solvents, i.e. fluorescence quantum yield (ΦF) is 61.9% in toluene and ΦF = 0.2% in methanol. Spin–orbit-coupled charge transfer-induced intersystem crossing (SOCT-ISC) was confirmed by femtosecond transient absorption spectroscopy (charge separation takes 1.7 ps and charge recombination takes 6.9 ns, in CH2Cl2). Nanosecond transient absorption spectra indicated the formation of perylene-localized triplet state, and the triplet state lifetime (175 μs) is much longer than that accessed with the heavy atom effect (3-bromoperylene; 16 μs). The singlet oxygen quantum (ΦΔ) yield of the dyad is 2.2% in hexane and 9.5% in dichloromethane. The low SOCT-ISC efficiency as compared to the previously reported analogue (ΦΔ = 80%) is attributed to the mismatch of the 1CT/Tn state energies, and/or the orientation of the NI and Py units, i.e. orthogonal geometry is not sufficient for achieving efficient SOCT-ISC in compact electron donor/acceptor dyads.

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Acknowledgements

X. Li thanks the NSFC (21576043) for financial support. J. Zhao thanks the NSFC (U2001222, 21673031, 21761142005 and 21911530095) and the State Key Laboratory of Fine Chemicals (ZYTS201901) for financial support.

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, E-208 West Campus, 2 Ling Gong Road, Dalian, 116024, People’s Republic of China

    Xi Chen, Muhammad Imran, Xiaolian Li & Jianzhang Zhao

  2. Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou, 515063, People’s Republic of China

    Junhong Pang & Mingde Li

  3. School of Chemistry and Key Laboratory of Energy Materials Chemistry, Ministry of Education, Institute of Applied Chemistry, Xinjiang University, UrumqiXinjiang, 830046, China

    Jianzhang Zhao

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  1. Xi Chen
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  2. Junhong Pang
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  3. Muhammad Imran
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  4. Xiaolian Li
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  5. Jianzhang Zhao
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  6. Mingde Li
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Correspondence to Xiaolian Li, Jianzhang Zhao or Mingde Li.

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Chen, X., Pang, J., Imran, M. et al. Charge separation, charge recombination and intersystem crossing in orthogonal naphthalimide–perylene electron donor/acceptor dyad. Photochem Photobiol Sci 20, 69–85 (2021). https://doi.org/10.1007/s43630-020-00002-w

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