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Title: Enhanced control of end-group composition in poly(3-hexylthiophene)s prepared by GRIM

Abstract

The ability to prepare well-defined semiconducting polymers is essential for understanding the link between structure and function in organic photovoltaic devices. A general method for enhanced control of the degree of functionality of end-functionalized poly(3-hexylthiophene)s (P3HT) prepared by Grignard Metathesis (GRIM) polymerization has been developed. In the absence of additives, the degree of functionality of end-functional P3HTs prepared by quenching of the GRIM polymerization with a Grignard reagent is dependent on the Grignard reagent utilized. In this study, additives such as styrene and 1-pentene are shown to alter the end-group composition of tolyl-functionalized P3HTs as determined by MALDI-TOF MS. In particular, when quenching the GRIM polymerization with tolylmagnesium bromide a modest decrease in the difunctional product is observed, and the yield of the monofunctional product increases significantly. Temperature and lithium chloride (LiCl) addition also play impactful roles. Monofunctional P3HT is found to be the major product (65%) when the functionalization is done in the presence of LiCl and styrene at 0oC, whereas in the absence of additives the monofunctional product is present at only 20%.

Authors:
 [1];  [1];  [1]
  1. ORNL
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Center for Nanophase Materials Sciences
Sponsoring Org.:
USDOE Laboratory Directed Research and Development (LDRD) Program
OSTI Identifier:
1044653
DOE Contract Number:  
DE-AC05-00OR22725
Resource Type:
Journal Article
Journal Name:
Journal of Polymer Science, Part A: Polymer Chemistry
Additional Journal Information:
Journal Volume: 50; Journal Issue: 14; Journal ID: ISSN 0887-624X
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ADDITIVES; BROMIDES; GRIGNARD REAGENTS; LITHIUM CHLORIDES; POLYMERIZATION; POLYMERS; QUENCHING; STYRENE

Citation Formats

Kochemba, William Michael, Kilbey, II, S Michael, and Pickel, Deanna L. Enhanced control of end-group composition in poly(3-hexylthiophene)s prepared by GRIM. United States: N. p., 2012. Web. doi:10.1002/pola.26057.
Kochemba, William Michael, Kilbey, II, S Michael, & Pickel, Deanna L. Enhanced control of end-group composition in poly(3-hexylthiophene)s prepared by GRIM. United States. doi:10.1002/pola.26057.
Kochemba, William Michael, Kilbey, II, S Michael, and Pickel, Deanna L. Sun . "Enhanced control of end-group composition in poly(3-hexylthiophene)s prepared by GRIM". United States. doi:10.1002/pola.26057.
@article{osti_1044653,
title = {Enhanced control of end-group composition in poly(3-hexylthiophene)s prepared by GRIM},
author = {Kochemba, William Michael and Kilbey, II, S Michael and Pickel, Deanna L},
abstractNote = {The ability to prepare well-defined semiconducting polymers is essential for understanding the link between structure and function in organic photovoltaic devices. A general method for enhanced control of the degree of functionality of end-functionalized poly(3-hexylthiophene)s (P3HT) prepared by Grignard Metathesis (GRIM) polymerization has been developed. In the absence of additives, the degree of functionality of end-functional P3HTs prepared by quenching of the GRIM polymerization with a Grignard reagent is dependent on the Grignard reagent utilized. In this study, additives such as styrene and 1-pentene are shown to alter the end-group composition of tolyl-functionalized P3HTs as determined by MALDI-TOF MS. In particular, when quenching the GRIM polymerization with tolylmagnesium bromide a modest decrease in the difunctional product is observed, and the yield of the monofunctional product increases significantly. Temperature and lithium chloride (LiCl) addition also play impactful roles. Monofunctional P3HT is found to be the major product (65%) when the functionalization is done in the presence of LiCl and styrene at 0oC, whereas in the absence of additives the monofunctional product is present at only 20%.},
doi = {10.1002/pola.26057},
journal = {Journal of Polymer Science, Part A: Polymer Chemistry},
issn = {0887-624X},
number = 14,
volume = 50,
place = {United States},
year = {2012},
month = {1}
}