Fully Fused Hydrazine-Embedded Nanographene with Near-Infrared Chiroptical Emission

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Abstract
Embedding hydrazine into graphenic networks, where two graphitic nitrogen atoms are directly linked by an N-N bond, endows unique redox activity and antiaromatic character, yet the construction of such fully fused architectures has remained a synthetic challenge. Here we report the first fully fused hydrazine-embedded nanographene (1) synthesized via a dehydrocyclization strategy. Single-crystal X-ray diffraction revealed a hydrazine moiety embedded within a fused polycyclic carbon framework measuring 1.4 nm diagonally with a helical saddle-shape. This π-extended architecture displays near-infrared (NIR) absorption (830 nm) and emission (879 nm, ΦF = 6.5%), as well as multistep redox processes accompanied by oxidation-induced planarization and an antiaromatic-to-aromatic transition. Chiral resolution further uncovered circularly polarized luminescence extending beyond 850 nm, which is observed for the first time from a helical nanographene. This study demonstrates that hydrazine embedment can be exploited to construct atomically precise nanocarbons with distinctive redox and NIR optical functions.
Funding Information
  • National Key Research and Development Program of China (2022YFA0912500)
  • Huaqiao University (23BS126)
  • Sanming Project of Medicine in Shenzen Municipality (SZSM202211022)
  • Science, Technology and Innovation Commission of Shenzhen Municipality (JCYJ20240813115805008, LCYSSQ20220823091403007, ZDSYS201707281114196)
  • Development and Reform Commission of Shenzhen Municipality
  • National Natural Science Foundation of China (22301188, 22571102, 52203335, 82192865, 82471186)
  • Shenzhen High-level Hospital Construction Fund
  • Shenzhen Portion of Shenzhen-Hong Kong Science and Technology Innovation Cooperation Zone (HTHZQSWS-KCCYB-2023060)

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