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A Modular Synthesis of Substituted Cycloparaphenylenes
Author(s) -
Kohrs Daniel,
Becker Jonathan,
Wegner Hermann A.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202104239
Subject(s) - synthon , geminal , aromatization , modular design , chemistry , van der waals force , block (permutation group theory) , ring (chemistry) , cycloaddition , stereochemistry , stacking , combinatorial chemistry , computer science , catalysis , molecule , organic chemistry , mathematics , combinatorics , operating system
Herein, we report a modular synthesis providing access to substituted cycloparaphenylenes (CPPs) of different sizes. A key synthon introducing two geminal ester units was efficiently prepared by [2+2+2] cycloaddition. This building block can be conveniently converted to macrocyclic precursors controlling the ring size of the final CPP. Efficient reductive aromatization through single‐electron transfer provided the substituted nanohoops in a straightforward manner. The t Bu ester substitution pattern enables a tube‐like arrangement in the solid‐state governed by van der Waals interactions that exhibits one of the tightest packings of CPPs in tube direction, thus opening new avenues in the crystal design of CPPs.