Short Fluoroalkanes Suppress a Thermally-Induced Phase Transition in a Layered Organic Crystal

Author:

Marjo Christopher E.1ORCID,Rich Anne M.1,Bhadbhade Mohan M.1,Bhattacharyya Saroj1,Yin Songyan1,Miskovic David M.2ORCID,Aldilla Vina R.3,Kumar Naresh3ORCID

Affiliation:

1. Mark Wainwright Analytical Centre, University of New South Wales, Kensington, NSW 2033, Australia

2. School of Materials Science and Engineering, University of New South Wales, Kensington, NSW 2033, Australia

3. School of Chemistry, University of New South Wales, Kensington, NSW 2033, Australia

Abstract

Ensuring a consistent crystal structure over a wide temperature range can be desirable behaviour in organic devices. This study investigates a layered crystal system formed by hydrogen-bonded chloro-s-triazine rings functionalised with alkyl or fluoroalkyl chains between the layers. When substituted with N-propyl groups (C3), the crystal undergoes a thermally-induced phase transition where the chains are ordered and bent below 170 K and disordered and extended above 175 K. Replacement with fluorinated N-propyl chains (C3-F) produces the same layered crystal but successfully suppresses the phase transition. The hydrocarbon and fluorocarbon analogues were found to be incompatible and unable to form co-crystals from solution or with mechanical mixing. Both effects were ascribed to more attractive C-F…F-C and C-H…F-C interactions in the fluorinated analogue. Long perfluoroalkanes are well known for controlling assembly in the solid state, but this study suggests that short-chain fluoroalkanes can exert strong control over the assembly and stability of an organic crystal.

Funder

Australian Research Council LIEF

Publisher

MDPI AG

Subject

Inorganic Chemistry,Condensed Matter Physics,General Materials Science,General Chemical Engineering

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