Organic Chemistry

Synthesis and Columnar Organization of Partially Fluorinated Dehydrobenz[18]annulenes

Authors

Abstract

Two diamond-shaped and partially fluorinated dehydrobenz[18]annulene macrocycles have been synthesized through a one-pot synthesis relying on fourfold Sonogashira coupling. Single crystal structures of the prepared macrocycles show continuous columnar stacks of these molecules that are mediated by the fluoroarene–alkyne, arene–alkyne, fluoroarene–fluoroarene, and alkyne–alkyne [π···π] interactions instead of the expected fluoroarene–arene [π···π] interaction.

Content

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Supplementary material

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Synthesis and Columnar Organization of Partially Fluorinated Dehydrobenz[18]annulenes
Synthetic procedure, NMR spectra, single crystal structures and analyses, computation analyses, and absorption and emission spectra of the DBAs.