Molecular-Simulation-Inspired Synthesis of [6]-Prismane via Photoisomerisation of Octafluoro[2.2]paracyclophane.

ABSTRACT: Prismanes have been attracting interest for nearly 50 years because of their geometric symmetry, highly strained structures, and unique applications due to their high carbon densities and bulky structures. Although [3]-, [4]-, and [5]-prismanes have been synthesised, [6]-prismanes and their derivatives remain elusive. Herein, fluorine chemistry, molecular mechanics, molecular orbital package, and density functional theory calculations were used to design and implement the photoisomerisation of octafluoro[2.2]paracyclophane (selected based on the good overlap of its lowest unoccupied molecular orbitals and short distance between the benzene rings) into octafluoro-[6]-prismane. Specifically, a dilute solution of the above precursor in CH₃CN/H₂O/dimethyl sulfoxide (DMSO)

SUBMITTER: Hosokawa Y 

PROVIDER: S-EPMC10891812 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature