Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs

Geoffrey E. Purdum; Nicholas G. Telesz; Karol Jarolimek; Sean M. Ryno; Thomas Gessner; Nicholas C. Davy; Anthony J. Petty; Yonggang Zhen; Ying Shu; Antonio Facchetti; Gavin E. Collis; Wenping Hu; Chao Wu; John E. Anthony; R. Thomas Weitz; Chad Risko; Yueh Lin Loo

doi:10.1021/jacs.8b01421

Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs

Geoffrey E. Purdum, Nicholas G. Telesz, Karol Jarolimek, Sean M. Ryno, Thomas Gessner, Nicholas C. Davy, Anthony J. Petty, Yonggang Zhen, Ying Shu, Antonio Facchetti, Gavin E. Collis, Wenping Hu, Chao Wu, John E. Anthony, R. Thomas Weitz, Chad Risko, Yueh Lin Loo

Chemistry

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

23 Scopus citations

Abstract

Polymorphism is pervasive in molecular solids. While computational predictions of the molecular polymorphic landscape have improved significantly, identifying which polymorphs are preferentially accessed and experimentally stable remains a challenge. We report a framework that correlates short intermolecular contacts with polymorphic stability. The presence of short contacts between neighboring molecules prevents structural rearrangement and stabilizes the packing arrangement, even when the stabilized polymorph is not enthalpically favored. In the absence of such intermolecular short contacts, the molecules have added degrees of freedom for structural rearrangement, and solid-solid polymorphic transformations occur readily. Starting with a series of core-halogenated naphthalene tetracarboxylic diimides, we establish this framework with the packing polymorphs of more than 20 compounds, ranging from molecular semiconductors to pharmaceutics and biological building blocks. This framework, widely applicable across molecular solids, can help refine computational predictions by identifying the polymorphs that are kinetically stable.

Original language	English
Pages (from-to)	7519-7525
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	140
Issue number	24
DOIs	https://doi.org/10.1021/jacs.8b01421
State	Published - Jun 20 2018

Bibliographical note

Funding Information:
A portion of this work was conducted at the Cornell High Energy Synchrotron Source (CHESS), which is supported by the National Science Foundation (NSF) under Award DMR-1332208. G.E.P. acknowledges financial support from the Department of Defense (DoD) through the National Defense Science and Engineering Graduate Fellowship (NDSEG) Program. G.E.P. and Y.-L.L. acknowledge NSF funding under Award DMR-1627453, as well as that from the Princeton Center for Complex Materials, a MRSEC supported by NSF under Award DMR-1420541. C.R. and J.E.A. acknowledge the NSF under Award DMR-1627428, and C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and Center for Computational Sciences (CCS).

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

Catalysis
Chemistry (all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b01421

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Purdum, G. E., Telesz, N. G., Jarolimek, K., Ryno, S. M., Gessner, T., Davy, N. C., Petty, A. J., Zhen, Y., Shu, Y., Facchetti, A., Collis, G. E., Hu, W., Wu, C., Anthony, J. E., Weitz, R. T., Risko, C., & Loo, Y. L. (2018). Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs. Journal of the American Chemical Society, 140(24), 7519-7525. https://doi.org/10.1021/jacs.8b01421

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title = "Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs",

abstract = "Polymorphism is pervasive in molecular solids. While computational predictions of the molecular polymorphic landscape have improved significantly, identifying which polymorphs are preferentially accessed and experimentally stable remains a challenge. We report a framework that correlates short intermolecular contacts with polymorphic stability. The presence of short contacts between neighboring molecules prevents structural rearrangement and stabilizes the packing arrangement, even when the stabilized polymorph is not enthalpically favored. In the absence of such intermolecular short contacts, the molecules have added degrees of freedom for structural rearrangement, and solid-solid polymorphic transformations occur readily. Starting with a series of core-halogenated naphthalene tetracarboxylic diimides, we establish this framework with the packing polymorphs of more than 20 compounds, ranging from molecular semiconductors to pharmaceutics and biological building blocks. This framework, widely applicable across molecular solids, can help refine computational predictions by identifying the polymorphs that are kinetically stable.",

author = "Purdum, {Geoffrey E.} and Telesz, {Nicholas G.} and Karol Jarolimek and Ryno, {Sean M.} and Thomas Gessner and Davy, {Nicholas C.} and Petty, {Anthony J.} and Yonggang Zhen and Ying Shu and Antonio Facchetti and Collis, {Gavin E.} and Wenping Hu and Chao Wu and Anthony, {John E.} and Weitz, {R. Thomas} and Chad Risko and Loo, {Yueh Lin}",

note = "Funding Information: A portion of this work was conducted at the Cornell High Energy Synchrotron Source (CHESS), which is supported by the National Science Foundation (NSF) under Award DMR-1332208. G.E.P. acknowledges financial support from the Department of Defense (DoD) through the National Defense Science and Engineering Graduate Fellowship (NDSEG) Program. G.E.P. and Y.-L.L. acknowledge NSF funding under Award DMR-1627453, as well as that from the Princeton Center for Complex Materials, a MRSEC supported by NSF under Award DMR-1420541. C.R. and J.E.A. acknowledge the NSF under Award DMR-1627428, and C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and Center for Computational Sciences (CCS). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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Purdum, GE, Telesz, NG, Jarolimek, K, Ryno, SM, Gessner, T, Davy, NC, Petty, AJ, Zhen, Y, Shu, Y, Facchetti, A, Collis, GE, Hu, W, Wu, C, Anthony, JE, Weitz, RT, Risko, C & Loo, YL 2018, 'Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs', Journal of the American Chemical Society, vol. 140, no. 24, pp. 7519-7525. https://doi.org/10.1021/jacs.8b01421

TY - JOUR

T1 - Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs

AU - Purdum, Geoffrey E.

AU - Telesz, Nicholas G.

AU - Jarolimek, Karol

AU - Ryno, Sean M.

AU - Gessner, Thomas

AU - Davy, Nicholas C.

AU - Petty, Anthony J.

AU - Zhen, Yonggang

AU - Shu, Ying

AU - Facchetti, Antonio

AU - Collis, Gavin E.

AU - Hu, Wenping

AU - Wu, Chao

AU - Anthony, John E.

AU - Weitz, R. Thomas

AU - Risko, Chad

AU - Loo, Yueh Lin

N1 - Funding Information: A portion of this work was conducted at the Cornell High Energy Synchrotron Source (CHESS), which is supported by the National Science Foundation (NSF) under Award DMR-1332208. G.E.P. acknowledges financial support from the Department of Defense (DoD) through the National Defense Science and Engineering Graduate Fellowship (NDSEG) Program. G.E.P. and Y.-L.L. acknowledge NSF funding under Award DMR-1627453, as well as that from the Princeton Center for Complex Materials, a MRSEC supported by NSF under Award DMR-1420541. C.R. and J.E.A. acknowledge the NSF under Award DMR-1627428, and C.R. thanks the University of Kentucky Vice President for Research for start-up funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the University of Kentucky Information Technology Department and Center for Computational Sciences (CCS). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/6/20

Y1 - 2018/6/20

N2 - Polymorphism is pervasive in molecular solids. While computational predictions of the molecular polymorphic landscape have improved significantly, identifying which polymorphs are preferentially accessed and experimentally stable remains a challenge. We report a framework that correlates short intermolecular contacts with polymorphic stability. The presence of short contacts between neighboring molecules prevents structural rearrangement and stabilizes the packing arrangement, even when the stabilized polymorph is not enthalpically favored. In the absence of such intermolecular short contacts, the molecules have added degrees of freedom for structural rearrangement, and solid-solid polymorphic transformations occur readily. Starting with a series of core-halogenated naphthalene tetracarboxylic diimides, we establish this framework with the packing polymorphs of more than 20 compounds, ranging from molecular semiconductors to pharmaceutics and biological building blocks. This framework, widely applicable across molecular solids, can help refine computational predictions by identifying the polymorphs that are kinetically stable.

AB - Polymorphism is pervasive in molecular solids. While computational predictions of the molecular polymorphic landscape have improved significantly, identifying which polymorphs are preferentially accessed and experimentally stable remains a challenge. We report a framework that correlates short intermolecular contacts with polymorphic stability. The presence of short contacts between neighboring molecules prevents structural rearrangement and stabilizes the packing arrangement, even when the stabilized polymorph is not enthalpically favored. In the absence of such intermolecular short contacts, the molecules have added degrees of freedom for structural rearrangement, and solid-solid polymorphic transformations occur readily. Starting with a series of core-halogenated naphthalene tetracarboxylic diimides, we establish this framework with the packing polymorphs of more than 20 compounds, ranging from molecular semiconductors to pharmaceutics and biological building blocks. This framework, widely applicable across molecular solids, can help refine computational predictions by identifying the polymorphs that are kinetically stable.

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DO - 10.1021/jacs.8b01421

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SP - 7519

EP - 7525

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ER -

Presence of Short Intermolecular Contacts Screens for Kinetic Stability in Packing Polymorphs

Abstract

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