Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization

Cheng Zhou; Qiuhong Cui; Caitlin McDowell; Martin Seifrid; Xiankai Chen; Jean Luc Brédas; Ming Wang; Fei Huang; Guillermo C. Bazan

doi:10.1002/anie.201702646

Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization

Cheng Zhou, Qiuhong Cui^*, Caitlin McDowell, Martin Seifrid, Xiankai Chen, Jean Luc Brédas, Ming Wang, Fei Huang, Guillermo C. Bazan

^*Corresponding author for this work

Physical Sciences and Engineering

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Two electronically delocalized molecules were designed as models to understand how molecular shape impacts the tradeoff between solubility and crystallization tendencies in molecular semiconductors. The more soluble compound TT contains a non-planar bithiophene central fragment, whereas CT has a planar cyclopentadithiophene unit. Calorimetry studies show that CT can crystallize more easily than TT. However, absorption spectroscopy shows that the initially amorphous TT film can eventually form crystals in which the molecular shape is significantly more planar. Two thermally reversible polymorphs for TT were observed by XRD and grazing-incidence wide-angle X-ray scattering (GIWAXS) measurements. These findings are relevant within the context of designing soft semiconductors that exhibit high solubility and a tendency to provide stable organized structures with desirable electronic properties.

Original language	English (US)
Pages (from-to)	9318-9321
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	32
DOIs	https://doi.org/10.1002/anie.201702646
State	Published - Aug 1 2017

Bibliographical note

Funding Information:
Work at UCSB was supported by the Office of Naval Research (ONR, Awards N00014-14-1-0580, N00014-16-1-2520, and N00014-17-1-2208) and the China Postdoctoral Science Foundation (No. 2016T90030). C. Z. and F. H. are supported by the Natural Science Foundation of China (No. 21520102006, 51603010, and 51521002). DFT studies at Georgia Tech were funded by the ONR (N00014-17-1-2208). XRD measurements were completed at the Materials Research Laboratory at UCSB, supported by NSF grant DMR-1121053. Use of the Stanford Synchrotron Radiation Lightsource, was supported by the Department of Energy, Office of Basic Energy Sciences (DE-AC02-76SF00515).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

conjugated molecules
crystallinity
molecular topology
organic semiconductors
solubility

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201702646

Cite this

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abstract = "Two electronically delocalized molecules were designed as models to understand how molecular shape impacts the tradeoff between solubility and crystallization tendencies in molecular semiconductors. The more soluble compound TT contains a non-planar bithiophene central fragment, whereas CT has a planar cyclopentadithiophene unit. Calorimetry studies show that CT can crystallize more easily than TT. However, absorption spectroscopy shows that the initially amorphous TT film can eventually form crystals in which the molecular shape is significantly more planar. Two thermally reversible polymorphs for TT were observed by XRD and grazing-incidence wide-angle X-ray scattering (GIWAXS) measurements. These findings are relevant within the context of designing soft semiconductors that exhibit high solubility and a tendency to provide stable organized structures with desirable electronic properties.",

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Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization

Abstract

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Keywords

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