Characterization of A π–π stacking cocrystal of 4-nitrophthalonitrile directed toward application in photocatalysis

Ting Xue, Cheng Ma, Le Liu, Chunhui Xiao (), Shao-Fei Ni () and Rong Zeng ()
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Ting Xue: Xi’an Jiaotong University
Cheng Ma: Shantou University
Le Liu: Xi’an Jiaotong University
Chunhui Xiao: Xi’an Jiaotong University
Shao-Fei Ni: Shantou University
Rong Zeng: Xi’an Jiaotong University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Photoexcitation of the electron-donor-acceptor complexes have been an effective approach to achieve radicals by triggering electron transfer. However, the catalytic version of electron-donor-acceptor complex photoactivation is quite underdeveloped comparing to the well-established utilization of electronically biased partners. In this work, we utilize 4-nitrophthalonitrile as an electron acceptor to facilitate the efficient π-stacking with electron-rich aromatics to form electron-donor-acceptor complex. The characterization and energy profiles on the cocrystal of 4-nitrophthalonitrile and 1,3,5-trimethoxybenzene disclose that the electron transfer is highly favorable under the light irradiation. This electron acceptor catalyst can be efficiently applied in the benzylic C−H bond photoactivation by developing the Giese reaction of alkylanisoles and the oxidation of the benzyl alcohols. A broad scope of electron-rich aromatics can be tolerated and a mechanism is also proposed. Moreover, the corresponding π-anion interaction of 4-nitrophthalonitrile with potassium formate can further facilitate the hydrocarboxylation of alkenes efficiently.

Date: 2024
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DOI: 10.1038/s41467-024-45686-1

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