ON/OFF Spiroconjugation through Peripheral Functionalization: Impact on the Reactivity and Chiroptical Properties of Spirobifluorenes

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Abstract

Spirobifluorenes are an important class of spiro compounds frequently used in the field of organic electronics. However, harnessing spiroconjugation to obtain high-performance in such structural motifs remains unexplored. We herein propose that peripheral functionalization may serve as a useful tool to control spiroconjugation in an ON/OFF manner on both chemical reactivity and photophysical properties. In particular, the ratio of mono- and di-functionalized spirobifluorenes found experimentally during their synthesis were found to be 3/2, 7/2, and 12/2 for phenyl, nitro-phenyl and amino-phenyl analogues, respectively. These remarkable reactivity differences correlate with the spiroconjugation character evaluated theoretically at the CAM-B3LYP/6-31G(d,p) level of theory. Additionally, comparison of experimental and predicted optical and chiroptical responses shows that spiroconjugated molecular orbitals have a significant or negligible involvement on the main electronic transitions depending on the peripheral functionality of the spirobifluorene.

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Ozcelik, A., Aranda, D., Pereira-Cameselle, R., Talavera, M., Covelo, B., Santoro, F., … Alonso-Gómez, J. L. (2022). ON/OFF Spiroconjugation through Peripheral Functionalization: Impact on the Reactivity and Chiroptical Properties of Spirobifluorenes. ChemPlusChem, 87(6). https://doi.org/10.1002/cplu.202100554

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