Influence of side-chain length and geometry on the thermal expansion behavior and polymorphism of naphthalene diimide-based thin films

Xuechen Jiao, Subashani Maniam, Steven J. Langford, Christopher R. McNeill

Research output: Contribution to journalArticleResearchpeer-review

Abstract

In this work, we report on the thermally induced phase behavior and crystalline structures of a series of solution-processable naphthalene diimide (NDI)-based molecules with alkyl side chains of varying length and branching. Taking advantage of synchrotron-based in situ grazing-incidence wide-angle x-ray scattering, the most kinetically favorable thin film crystalline structures of each molecule at room temperature and at elevated temperatures were resolved. The extracted unit cell parameters of the kinetically favorable crystal structures as a function of temperature were used to quantify the anisotropic thermal expansion coefficients along the three principal crystallographic directions. In particular, it is found that long alkyl side chains can effectively suppress crystalline polymorphism and enhance thermal reversibility. The acquired knowledge regarding the thermally induced phase transitions of thin films based on NDI-based small molecules with varying solubilizing side chains serves as guidance for further molecular design and synthesis of high performance n-type small molecules.

Original languageEnglish
Article number013606
Number of pages11
JournalPhysical Review Materials
Volume3
Issue number1
DOIs
Publication statusPublished - 14 Jan 2019

Cite this

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abstract = "In this work, we report on the thermally induced phase behavior and crystalline structures of a series of solution-processable naphthalene diimide (NDI)-based molecules with alkyl side chains of varying length and branching. Taking advantage of synchrotron-based in situ grazing-incidence wide-angle x-ray scattering, the most kinetically favorable thin film crystalline structures of each molecule at room temperature and at elevated temperatures were resolved. The extracted unit cell parameters of the kinetically favorable crystal structures as a function of temperature were used to quantify the anisotropic thermal expansion coefficients along the three principal crystallographic directions. In particular, it is found that long alkyl side chains can effectively suppress crystalline polymorphism and enhance thermal reversibility. The acquired knowledge regarding the thermally induced phase transitions of thin films based on NDI-based small molecules with varying solubilizing side chains serves as guidance for further molecular design and synthesis of high performance n-type small molecules.",
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Influence of side-chain length and geometry on the thermal expansion behavior and polymorphism of naphthalene diimide-based thin films. / Jiao, Xuechen; Maniam, Subashani; Langford, Steven J.; McNeill, Christopher R.

In: Physical Review Materials, Vol. 3, No. 1, 013606, 14.01.2019.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Influence of side-chain length and geometry on the thermal expansion behavior and polymorphism of naphthalene diimide-based thin films

AU - Jiao, Xuechen

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AU - McNeill, Christopher R.

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AB - In this work, we report on the thermally induced phase behavior and crystalline structures of a series of solution-processable naphthalene diimide (NDI)-based molecules with alkyl side chains of varying length and branching. Taking advantage of synchrotron-based in situ grazing-incidence wide-angle x-ray scattering, the most kinetically favorable thin film crystalline structures of each molecule at room temperature and at elevated temperatures were resolved. The extracted unit cell parameters of the kinetically favorable crystal structures as a function of temperature were used to quantify the anisotropic thermal expansion coefficients along the three principal crystallographic directions. In particular, it is found that long alkyl side chains can effectively suppress crystalline polymorphism and enhance thermal reversibility. The acquired knowledge regarding the thermally induced phase transitions of thin films based on NDI-based small molecules with varying solubilizing side chains serves as guidance for further molecular design and synthesis of high performance n-type small molecules.

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