Carbodicarbene Derived Extremely Electron-Rich C(sp³)-C(sp³) Bonds Anukul Jana Tata Institute of Fundamental Research Hyderabad, India The carbon-carbon sigma (σ) bond in alkanes is constituted by the head-on overlap of two C- sp 3 -orbitals. As a result, the removal of σ-electrons from the sigma bond of alkanes are not easy unlike the removal of π-electrons from a π -bond (π-bond is constituted by the lateral overlap of two p -orbitals) of alkenes. 1 However, there are reports in removing electrons from the electron-rich carbon-carbon sigma (σ) bond carrying substituents like (per)-aryl, (di)-amino at the alkanyl carbons. 2 Moreover, some of these electron-rich carbon-carbon sigma bonded compounds have been utilized as n-dopant in conjugated polymers. 3 In my poster I would like to showcase the rationally designed compounds possessing electron-rich carbon-carbon sigma (σ) bond having E 1/2 = −1.17 V and −0.91 V vs. Fc/Fc + , considering the reduction of conjugate acids of NHC/NHC and NHC/CAAC-based carbones. 4 Also I will showcase our recent finding to developed other electron-rich carbon-carbon sigma bonds. 5 References 1. V. G. Nenajdenko, N. E. Shevchenko, E. S. Balenkova and I. V. Alabugin, Chem. Rev., 2003, 103 , 229–282. 2. T. Shimajiri, T. Suzuki and Y. Ishigaki, Angew. Chem., Int. Ed., 2020, 59 , 22252–22257. 3. ( a ) S. Zhang, B. D. Naab, E. V. Jucov, S. Parkin, E. G. B. Evans, G. L. Millhauser, T. V. Timofeeva, C. Risko, J.-L. Brédas, Z. Bao, S. Barlow and S. R. Marder, Chem. Eur. J., 2015, 21 , 10878–10885; ( b ) Y. Lu, J.-Y. Wang and J. Pei, Acc. Chem. Res., 2021, 54 , 2871–2883. 4. R. Dolai, R. Kumar, B. J. Elvers, P. K. Pal, B. Joseph, R. Sikari, M. K. Nayak, A. Maiti, T. Singh, N. Chrysochos, A. Jayaraman, I. Krummenacher, J. Mondal, U. D. Priyakumar, H. Braunschweig, C. B. Yildiz, C. Schulzke and A. Jana, Chem. Eur. J., 2023 , 29 , e202202888. 5. M. K. Nayak, B. J. Elvers, D. Mandal, A. Das, R. Ramakrishnan, K. R. Mote, C. Schulzke, C. B. Yildiz and A. Jana, Chem. Commun., 2023, 59 , 6698–6701.
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