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Cumulene Rotaxanes: Stabilization and Study of [9]Cumulenes
Author(s) -
Franz Michael,
Januszewski Johanna A.,
Wendinger Dominik,
Neiss Christian,
Movsisyan Levon D.,
Hampel Frank,
Anderson Harry L.,
Görling Andreas,
Tykwinski Rik R.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501810
Subject(s) - cumulene , steric effects , chemistry , differential scanning calorimetry , polymer chemistry , photochemistry , stereochemistry , molecule , organic chemistry , physics , thermodynamics
The stabilization of long [ n ]cumulenes has traditionally been achieved by placing sterically bulky “protecting groups” at the termini, which shield the reactive carbon chain from unwanted reactions. Herein, we present an alternative strategy: stabilization through threading the sp‐hybridized carbon chain through a phenanthroline‐based macrocycle. The result is stable [9]cumulene rotaxanes that enable the study of properties as a function of length for [ n ]cumulenes in unprecedented detail, including by quantitative UV/Vis spectroscopy, cyclic voltammetry, and differential scanning calorimetry. The experimental results are supported by DFT calculations.
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