Controlled Generation of 9-Boratriptycene by Lewis Adduct Dissociation: Accessing a Non‐Planar Triarylborane

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Abstract

A highly bent triarylborane, 9-boratriptycene, was generated in solution by selective protodeboronation of the corresponding tetra-aryl boron ate complex with the strong Brønsted acid HNTf2. The iptycene core confers enhanced Lewis acidity to 9-boratriptycene, making it unique in terms of structure and reactivity. We studied the stereoelectronic properties of 9-boratriptycene by quantifying its association with small N- and O-centered Lewis bases, as well as with sterically hindered phosphines. The resultant Lewis adducts exhibited unique structural, spectroscopic, and photophysical properties. Beyond the high pyramidalization of the 9-boratriptycene scaffold and its low reorganization energy upon Lewis base coordination, quantum chemical calculations revealed that the absence of π donation from the triptycene aryl rings to the boron vacant pz orbital is one of the main reasons for its high Lewis acidity.

Original languageEnglish
Article number10.1002/ange.202003119
Pages (from-to)12502-12506
Number of pages5
JournalAngewandte Chemie
Volume132
Issue number30
DOIs
Publication statusPublished - 20 Jul 2020

Keywords

  • Lewis adducts
  • non-planar boron Lewis acids
  • triarylborane
  • triptycene

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    Synthesis of sterically hindered phosphatriptycenes and computational investigation of their properties in the context of frustrated lewis pair chemistry

    Author: Mahaut, D., 1 Feb 2019

    Supervisor: Berionni, G. (Supervisor) & Champagne, B. (Co-Supervisor)

    Student thesis: Master typesMaster in Chemistry Research focus

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