NDLI: Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT

Content Provider	Royal Society of Chemistry (RSC)
Author	Bazan, Guillermo C. Ford, Michael Mai, Cheng-Kang Coughlin, Jessica Fronk, Stephanie L. Wang, Ming
Copyright Year	2016
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.
Starting Page	5313
Ending Page	5321
Page Count	9
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	8
Journal	Chemical Science
DOI	10.1039/c6sc00908e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Spectroscopy Polymer Substituent Nitrogen Biomolecular structure Molecular geometry Circular dichroism Racemic mixture Pyridine Anisotropy Chirality Alkane stereochemistry Conformational isomerism Optical rotation Band gap Solvent
Content Type	Text
Resource Type	Article
Subject	Chemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities

Secondary structure formation of main-chain chiral poly(2-oxazoline)s in solution

Unusual solvent effects on chiroptical properties of an optically active regioregular polythiophene in solution

Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS

Absolute configurational assignment in chiral compounds through vibrational circular dichroism (vcd) spectroscopy.

Enantioseparation on poly(phenyl isocyanide)s with macromolecular helicity memory as chiral stationary phases for HPLC

Inducing Propeller Chirality in Triaryl Boranes with Chiral Amines.

Molecular chirality detection using plasmonic and dielectric nanoparticles

Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT

Similar Documents

Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities

Secondary structure formation of main-chain chiral poly(2-oxazoline)s in solution

Unusual solvent effects on chiroptical properties of an optically active regioregular polythiophene in solution

Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

CHIRAL CHROMATOGRAPHIC ANALYSIS AND ABSOLUTE STEREOCHEMISTRY OF RACEMIC CHLORPHENERAMINE USING CHIRAL HPLC-CD-OR AND TD-DFT CALCULATIONS

Absolute configurational assignment in chiral compounds through vibrational circular dichroism (vcd) spectroscopy.

Enantioseparation on poly(phenyl isocyanide)s with macromolecular helicity memory as chiral stationary phases for HPLC

Inducing Propeller Chirality in Triaryl Boranes with Chiral Amines.

Molecular chirality detection using plasmonic and dielectric nanoparticles

Effect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT