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

Chemical Science
Stephanie L FronkGuillermo C Bazan

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 nitroge...Continue Reading

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Citations

Jun 22, 2018·Nature Communications·Matthias SchulzManuela Schiek
Apr 10, 2018·Chemical Reviews·Jorge G IbanezBernardo A Frontana-Uribe
Sep 8, 2020·Chemical Reviews·Gianluigi AlbanoLorenzo Di Bari
Apr 4, 2019·Chemical Reviews·Flavia PopNarcis Avarvari

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Methods Mentioned

BETA
differential scanning calorimetry
circular dichroism
atomic
X-ray
AFM

Software Mentioned

GIWAXS

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