Dissecting Porosity in Molecular Crystals: Influence of Geometry, Hydrogen Bonding, and [π···π] Stacking on the Solid-State Packing of Fluorinated Aromatics

doi:10.1021/jacs.8b02869

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Title:	Dissecting Porosity in Molecular Crystals: Influence of Geometry, Hydrogen Bonding, and [π···π] Stacking on the Solid-State Packing of Fluorinated Aromatics
Authors:	Mohamed I. Hashim;Ha T. M. Le;Teng-Hao Chen;Yu-Sheng Chen;Olafs Daugulis;Chia-Wei Hsu;Allan J. Jacobson;Watchareeya Kaveevivitchai;Xiao Liang;Tatyana Makarenko;Ognjen Š. Miljanić;Ilja Popovs;Hung Vu Tran;Xiqu Wang;Chia-Hua Wu;Judy I. Wu
Date:	2018-04-14
Issue Date:	2018-05-18 12:10:23 (UTC+8)
Abstract:	Porous molecular crystals are an emerging class of porous materials that is unique in being built from discrete molecules rather than being polymeric in nature. In this study, we examined the effects of molecular structure of the precursors on the formation of porous solid-state structures with a series of 16 rigid aromatics. The majority of these precursors possess pyrazole groups capable of hydrogen bonding, as well as electron-rich aromatics and electron-poor tetrafluorobenzene rings. These precursors were prepared using a combination of Pd- and Cu-catalyzed cross-couplings, careful manipulations of protecting groups on the nitrogen atoms, and solvothermal syntheses. Our study varied the geometry and dimensions of precursors, as well as the presence of groups capable of hydrogen bonding and [π···π] stacking. Thirteen derivatives were crystallographically characterized, and four of them were found to be porous with surface areas between 283 and 1821 m2 g–1. Common to these four porous structures were (a) rigid trigonal geometry, (b) [π···π] stacking of electron-poor tetrafluorobenzenes with electron-rich pyrazoles or tetrazoles, and (c) hydrogen bonding between the terminal heteroaromatic rings.
Relation:	Journal of the American Chemical Society 140(18), p.6014-6026
DOI:	10.1021/jacs.8b02869
Appears in Collections:	[Graduate Institute & Department of Chemistry] Journal Article

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