Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT
Abstract
Two narrow bandgap conjugated polymers containing chiral 2-ethylhexyl side chains were synthesized: poly[(4,4-bis(2-ethylhexyl)cyclopenta-[2,1-b:3,4-b']dithiophene)-2,6-diyl-alt-(2,1,3-benzothiadiazole)-4,7-diyl] (PCPDTBT*) and poly[(4,4-bis(2-ethylhexyl)cyclopenta[2,1-b:3,4-b0]dithiophene)-2,6-diyl-alt-[1,2,5]-thiadiazolo[3,4-c]pyridine] (PCDTPT*). The presence of a chiral substituent provides a handle to study the geometry of interchain aggregates and/or the secondary structure of these conjugated polymers in solution and in thin films via circular dichroism (CD) spectroscopy, provided that the asymmetry in the side-chain is translated to the optically active conjugated backbone. CD signals are observed for PCPDTBT* and PCDTPT* in poor solvent systems, which indicate the presence of chiral ordering in the aggregates. PCPDTBT* shows greater chiral order than PCDTPT* based on their relative anisotropy factors. Additionally, GIWAXS analysis reveals that PCPDTBT* films are more ordered than what is observed for the same polymer containing racemic 2-ethylhexyl chains. Upon solution deposition, the chiral ordering is found to translate to the solid-state microstructure for PCPDTBT* but not PCDTPT*. The presence of a pyridyl nitrogen on the thiadiazolo[3,4-c]pyridine ring of PCDTPT* favors a planar conformation for the backbone such that it has a higher rotational barrier compared to PCPDTBT*. This larger rotational barrier appears to limit the ability of PCDTPT* to adopt a helical structure or relevant chain distortions for achieving chiral aggregates.
- Authors:
-
[1];
- Univ. of California, Santa Barbara, CA (United States)
- Univ. of California, Santa Barbara, CA (United States); King Abdulaziz University, Jeddah (Saudi Arabia)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 1624937
- Grant/Contract Number:
- AC02-76SF00515; DMR1411240; DMR 1121053; CNS-0960316
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Volume: 7; Journal Issue: 8; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry
Citation Formats
Fronk, Stephanie L., Wang, Ming, Ford, Michael, Coughlin, Jessica, Mai, Cheng-Kang, and Bazan, Guillermo C. Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT. United States: N. p., 2016.
Web. doi:10.1039/c6sc00908e.
Fronk, Stephanie L., Wang, Ming, Ford, Michael, Coughlin, Jessica, Mai, Cheng-Kang, & Bazan, Guillermo C. Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT. United States. https://doi.org/10.1039/c6sc00908e
Fronk, Stephanie L., Wang, Ming, Ford, Michael, Coughlin, Jessica, Mai, Cheng-Kang, and Bazan, Guillermo C. Tue .
"Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT". United States. https://doi.org/10.1039/c6sc00908e. https://www.osti.gov/servlets/purl/1624937.
@article{osti_1624937,
title = {Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT},
author = {Fronk, Stephanie L. and Wang, Ming and Ford, Michael and Coughlin, Jessica and Mai, Cheng-Kang and Bazan, Guillermo C.},
abstractNote = {Two narrow bandgap conjugated polymers containing chiral 2-ethylhexyl side chains were synthesized: poly[(4,4-bis(2-ethylhexyl)cyclopenta-[2,1-b:3,4-b']dithiophene)-2,6-diyl-alt-(2,1,3-benzothiadiazole)-4,7-diyl] (PCPDTBT*) and poly[(4,4-bis(2-ethylhexyl)cyclopenta[2,1-b:3,4-b0]dithiophene)-2,6-diyl-alt-[1,2,5]-thiadiazolo[3,4-c]pyridine] (PCDTPT*). The presence of a chiral substituent provides a handle to study the geometry of interchain aggregates and/or the secondary structure of these conjugated polymers in solution and in thin films via circular dichroism (CD) spectroscopy, provided that the asymmetry in the side-chain is translated to the optically active conjugated backbone. CD signals are observed for PCPDTBT* and PCDTPT* in poor solvent systems, which indicate the presence of chiral ordering in the aggregates. PCPDTBT* shows greater chiral order than PCDTPT* based on their relative anisotropy factors. Additionally, GIWAXS analysis reveals that PCPDTBT* films are more ordered than what is observed for the same polymer containing racemic 2-ethylhexyl chains. Upon solution deposition, the chiral ordering is found to translate to the solid-state microstructure for PCPDTBT* but not PCDTPT*. The presence of a pyridyl nitrogen on the thiadiazolo[3,4-c]pyridine ring of PCDTPT* favors a planar conformation for the backbone such that it has a higher rotational barrier compared to PCPDTBT*. This larger rotational barrier appears to limit the ability of PCDTPT* to adopt a helical structure or relevant chain distortions for achieving chiral aggregates.},
doi = {10.1039/c6sc00908e},
journal = {Chemical Science},
number = 8,
volume = 7,
place = {United States},
year = {Tue May 03 00:00:00 EDT 2016},
month = {Tue May 03 00:00:00 EDT 2016}
}
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