: We present a divergent synthetic approach to C2-symmetrical 3,4-Ethylenedioxythiophene (EDOT) monomers in which functionalities can be introduced as pendant chains from the ethylene bridge. The key synthon, obtained through a high yielding trans-etherification, is the chiral EDOT with bromomethyl pendant groups and is prone to substitution reactions with oxygen-based nucleophiles. Elimination of the key precursor affords a diene that can be elaborated into unprecedented PhEDOT monomers using the Diels-Alder reaction. The strategy is further validated by the synthesis of a dithiane-containing EDOT.
C2-Symmetrical 3,4-Ethylenedioxythiophene Monomers through a Divergent Approach
Martinelli, Angelo;Nitti, Andrea;Pasini, Dario
2024-01-01
Abstract
: We present a divergent synthetic approach to C2-symmetrical 3,4-Ethylenedioxythiophene (EDOT) monomers in which functionalities can be introduced as pendant chains from the ethylene bridge. The key synthon, obtained through a high yielding trans-etherification, is the chiral EDOT with bromomethyl pendant groups and is prone to substitution reactions with oxygen-based nucleophiles. Elimination of the key precursor affords a diene that can be elaborated into unprecedented PhEDOT monomers using the Diels-Alder reaction. The strategy is further validated by the synthesis of a dithiane-containing EDOT.File in questo prodotto:
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