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Title: Conjugated ladder polymers by a cyclopentannulation polymerization

Here, we report a nontraditional synthesis of cyclopentafused-polycyclic aromatic hydrocarbon embedded ladder polymers using a palladium catalyzed cyclopentannulation polymerization followed by a cyclodehydrogenation reaction. Donor–acceptor type polymers containing a cyclopenta[hi]aceanthrylene acceptor groups can be synthesized by a palladium catalyzed copolymerization between 9,10-dibromoanthracene and a variety of bis(arylethynyl)arenes to give polymers with molecular weights (Mn) of 9–22 kDa. The bis(arylethynyl)arenes were composed of benzene, thiophene, or thieno[3,2- b]thiophene moieties, which provided access to a series of four donor–acceptor copolymers. The polymers were subjected to cyclodehydrogenation with FeCl 3 to access rigid ladder type polymers with the conversion investigated by 13C NMR of isotopically labeled polymers. As a result, the ladder polymers possess broad UV–Vis absorptions and narrow optical band gaps of 1.17–1.29 eV and are p-type semiconductors in organic field effect transistors.
Authors:
 [1] ;  [1] ;  [2] ; ORCiD logo [2] ; ORCiD logo [1]
  1. Southern Illinois Univ., Carbondale, IL (United States)
  2. Argonne National Lab. (ANL), Argonne, IL (United States)
Publication Date:
Grant/Contract Number:
AC02-06CH11357
Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 139; Journal Issue: 16; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Research Org:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Scientific User Facilities Division; National Science Foundation (NSF)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1364137

Bheemireddy, Sambasiva R., Hautzinger, Matthew P., Li, Tao, Lee, Byeongdu, and Plunkett, Kyle N.. Conjugated ladder polymers by a cyclopentannulation polymerization. United States: N. p., Web. doi:10.1021/jacs.6b12916.
Bheemireddy, Sambasiva R., Hautzinger, Matthew P., Li, Tao, Lee, Byeongdu, & Plunkett, Kyle N.. Conjugated ladder polymers by a cyclopentannulation polymerization. United States. doi:10.1021/jacs.6b12916.
Bheemireddy, Sambasiva R., Hautzinger, Matthew P., Li, Tao, Lee, Byeongdu, and Plunkett, Kyle N.. 2017. "Conjugated ladder polymers by a cyclopentannulation polymerization". United States. doi:10.1021/jacs.6b12916. https://www.osti.gov/servlets/purl/1364137.
@article{osti_1364137,
title = {Conjugated ladder polymers by a cyclopentannulation polymerization},
author = {Bheemireddy, Sambasiva R. and Hautzinger, Matthew P. and Li, Tao and Lee, Byeongdu and Plunkett, Kyle N.},
abstractNote = {Here, we report a nontraditional synthesis of cyclopentafused-polycyclic aromatic hydrocarbon embedded ladder polymers using a palladium catalyzed cyclopentannulation polymerization followed by a cyclodehydrogenation reaction. Donor–acceptor type polymers containing a cyclopenta[hi]aceanthrylene acceptor groups can be synthesized by a palladium catalyzed copolymerization between 9,10-dibromoanthracene and a variety of bis(arylethynyl)arenes to give polymers with molecular weights (Mn) of 9–22 kDa. The bis(arylethynyl)arenes were composed of benzene, thiophene, or thieno[3,2-b]thiophene moieties, which provided access to a series of four donor–acceptor copolymers. The polymers were subjected to cyclodehydrogenation with FeCl3 to access rigid ladder type polymers with the conversion investigated by 13C NMR of isotopically labeled polymers. As a result, the ladder polymers possess broad UV–Vis absorptions and narrow optical band gaps of 1.17–1.29 eV and are p-type semiconductors in organic field effect transistors.},
doi = {10.1021/jacs.6b12916},
journal = {Journal of the American Chemical Society},
number = 16,
volume = 139,
place = {United States},
year = {2017},
month = {4}
}