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3. Ultrafast Exciton Trapping at sp ³ Quantum Defects in Carbon Nanotubes

   https://doi.org/10.1021/acsnano.9b06279  

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5. A Strongly Reducing sp ² Carbon‐Conjugated Covalent Organic Framework Formed by N ‐Heterocyclic Carbene Dimerization

   https://doi.org/10.1002/anie.202416480  

   Pitt, Tristan_A; Azbell, Tyler_J; Kim, Jaehwan; Shi, Zixiao; Muller, David_A; Addicoat, Matthew_A; Milner, Phillip_J (October 2024, Angewandte Chemie International Edition)

   Abstract Covalent organic frameworks linked by carbon‐carbon double bonds (C=C COFs) are an emerging class of crystalline, porous, and conjugated polymeric materials with potential applications in organic electronics, photocatalysis, and energy storage. Despite the rapidly growing interest in sp²carbon‐conjugated COFs, only a small number of closely related condensation reactions have been successfully employed for their synthesis to date. Herein, we report the first example of a C=C COF, CORN‐COF‐1 (CORN=Cornell University), prepared byN‐heterocyclic carbene (NHC) dimerization. In‐depth characterization reveals that CORN‐COF‐1 possesses a two‐dimensional layered structure and hexagonal guest‐accessible pores decorated with a high density of strongly reducing tetraazafulvalene linkages. Exposure of CORN‐COF‐1 to tetracyanoethylene (TCNE,E_1/2=0.13 V and −0.87 V vs. SCE) oxidizes the COF and encapsulates the radical anion TCNE⋅⁻and the dianion TCNE²⁻as guest molecules, as confirmed by spectroscopic and magnetic analysis. Notably, the reactive TCNE⋅⁻radical anion, which generally dimerizes in the solid state, is uniquely stabilized within the pores of CORN‐COF‐1. Overall, our findings broaden the toolbox of reactions available for the synthesis of redox‐active C=C COFs, paving the way for the design of novel materials. 

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