Dithiophenylpyrrole derivative monomers for preparing semi-condu

Details Dithiophenylpyrrole derivative monomers for preparing semi-condu Dithiophenylpyrrole derivative monomers for preparing semi-condu

1989-03-31

1991-06-04

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

528380, 252500, C07D40914

Patent

active

050215868

ABSTRACT:
The present invention relates to a number of innovative electrophilic substitution reactions involving 2,5-dithienylpyrrole (2,5-DTP). More specifically, these reactions are used in the synthesis of monomers for preparing functionalized conducting organic polymers.
The elctrophilic substitution reactions in this invention are accomplished under conditions not requiring the use of N-1 pyrrole blocking groups to direction reaction at the pyrrole C-3 position. This is because the steric bulk of the 2,5-dithienyl groups prevent N-acylation and therefore direct reactions with electrophiles at the pyrrole C-3 position.
The reaction conditions chosen have also demonstrated a greater regioselectively towards functionalization at the pyrrole 3-position than the basic reaction conditions suggested in the prior art. This result may be explained by an activation of the pyrrole 3-position towards electrophilic substitution. This is attributed to an electron donating resonance contribution of the 2,5 thienyl groups.
Other advantageous reaction conditions have been discovered which direct electrophilic substitution preferentially at the pyrrole or thiophene groups depending upon the amount of acidic catalyst.

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