Bowl-Direction Control of Monofluorosumanene in the Solid State

24 August 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A new curved π-conjugated molecule-1-fluorosumanene (1) was designed and synthesized which possesses one fluorine atom on the benzylic carbon of sumanene. This compound is able to exhibit bowl inversion in solution, leading to the formation of two diastere-omers 1endo and 1exo with different dipole moment. Experimental and theoretical investigation revealed energetical relationship among 1exo, 1endo and solvent to realize the control of exo:endo ratio in the single crystals of 1 by the correct choice of the crystalliza-tion solvent. Significantly, the molecular dynamics (MD) simulations revealed that 1exo positively worked for elongation of the stacking structure and the final exo:endo ratio was affected by the relative stability difference between 1endo and 1exo derived by solv-ation. Such controllable exo:endo ratio of 1 realized the preparation of unique materials showing totally different dielectric response from the same molecule 1 just by changing crystallization solvent.


Bowl inversion
Crystal Engineering
Solvent Effect
Dielectric Property

Supplementary materials

Supporting Information
Synthesis of 1, the detailed experimental procedures, single crys-tal X-ray analysis, computational procedure and the supplemental figures.


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