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

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

12 Citations (Scopus)

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
Pages (from-to)	9318-9321
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	32
DOIs	https://doi.org/10.1002/anie.201702646
Publication status	Published - 1 Aug 2017
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Research Keywords

conjugated molecules
crystallinity
molecular topology
organic semiconductors
solubility

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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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AU - Seifrid, Martin

AU - Chen, Xiankai

AU - Brédas, Jean-Luc

AU - Wang, Ming

AU - Huang, Fei

AU - Bazan, Guillermo C.

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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AB - 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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KW - molecular topology

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Topological Transformation of π-Conjugated Molecules Reduces Resistance to Crystallization

Abstract

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