A high-pressure polymorph of the organic semiconductor rubrene was obtained above 6.0 GPa by hydrostatic compression of the triclinic form. In the high-pressure phase, rubrene adopts an unexpected and previously unobserved conformation, which is ca. 70 kJ/mol less stable than the planar one observed in the ambient-pressure phase and is characterized by a unique "double twisting" of the tetracene core and "scissoring" of the lateral phenyl groups, which favor the formation of C-H center dot center dot center dot pi contacts. The evolution of the structure as a function of pressure is monitored and quantified by Hirshfeld surfaces analysis and calculations of lattice and intermolecular interaction energies. The isosymmetric single-crystal-to-single-crystal transition is fully reversible and is primarily driven by a reduction in molecular volume.

Bergantin, S., Moret, M., Buth, G., Fabbiani, F. (2014). Pressure-Induced Conformational Change in Organic Semiconductors: Triggering a Reversible Phase Transition in Rubrene. JOURNAL OF PHYSICAL CHEMISTRY. C., 118(25), 13476-13483 [10.1021/jp503271h].

Pressure-Induced Conformational Change in Organic Semiconductors: Triggering a Reversible Phase Transition in Rubrene

MORET, MASSIMO
Secondo
;
2014

Abstract

A high-pressure polymorph of the organic semiconductor rubrene was obtained above 6.0 GPa by hydrostatic compression of the triclinic form. In the high-pressure phase, rubrene adopts an unexpected and previously unobserved conformation, which is ca. 70 kJ/mol less stable than the planar one observed in the ambient-pressure phase and is characterized by a unique "double twisting" of the tetracene core and "scissoring" of the lateral phenyl groups, which favor the formation of C-H center dot center dot center dot pi contacts. The evolution of the structure as a function of pressure is monitored and quantified by Hirshfeld surfaces analysis and calculations of lattice and intermolecular interaction energies. The isosymmetric single-crystal-to-single-crystal transition is fully reversible and is primarily driven by a reduction in molecular volume.
Articolo in rivista - Articolo scientifico
CRYSTAL STRUCTURE; INTERMOLECULAR INTERACTIONS; MOLECULAR-CRYSTALS; POLYMORPHS; HIGH PRESSURE; ORGANIC SEMICONDUCTORS; FILMS
English
2014
118
25
13476
13483
none
Bergantin, S., Moret, M., Buth, G., Fabbiani, F. (2014). Pressure-Induced Conformational Change in Organic Semiconductors: Triggering a Reversible Phase Transition in Rubrene. JOURNAL OF PHYSICAL CHEMISTRY. C., 118(25), 13476-13483 [10.1021/jp503271h].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/81119
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