Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

Michael A Sinnwell; Eric W Reinheimer; Davide M Proserpio; Leonard Macgillivray; Shalisa M Oburn; Devin P Ericson; Ryan H Groeneman

doi:10.1107/S2052252519011382

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Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

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Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

Michael A Sinnwell, Eric W Reinheimer, Davide M Proserpio, Leonard Macgillivray, Shalisa M Oburn, Devin P Ericson and Ryan H Groeneman

IUCrJ, Vol.6(Pt 6), pp.1032-1039

08/13/2019

DOI: 10.1107/S2052252519011382

PMCID: PMC6830215

PMID: 31709059

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Abstract

A three-dimensional hydrogen-bonded network based on a rare mok topology has been constructed using an organic molecule synthesized in the solid state. The molecule is obtained using a supramolecular protecting-group strategy that is applied to a solid-state [2+2] photodimerization. The photodimerization affords a novel head-to-head cyclobutane product. The cyclobutane possesses tetrahedrally disposed cis-hydrogen-bond donor (phenolic) and cis-hydrogen-bond acceptor (pyridyl) groups. The product self-assembles in the solid state to form a mok network that exhibits twofold interpenetration. The cyclobutane adopts different conformations to provide combinations of hydrogen-bond donor and acceptor sites to conform to the structural requirements of the mok net.

bonded organic networks

Chimica Generale e Inorganica

crystal engineering

crystals

dimensional hydrogen

intermolecular interactions

organic solid

photocycloaddition

Research Papers

Science

Settore CHIM

state reactions

supramolecular chemistry

three

Details

Title: Subtitle: Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds
Creators: Michael A Sinnwell
Eric W Reinheimer
Davide M Proserpio
Leonard Macgillivray
Shalisa M Oburn
Devin P Ericson
Ryan H Groeneman
Resource Type: Journal article
Publication Details: IUCrJ, Vol.6(Pt 6), pp.1032-1039
DOI: 10.1107/S2052252519011382
PMID: 31709059
PMCID: PMC6830215
NLM abbreviation: IUCrJ
ISSN: 2052-2525
eISSN: 2052-2525
Publisher: International Union of Crystallography
Grant note: DOI: 10.13039/501100008982, name: National Science Foundation, award: DMR-1708673; DOI: 10.13039/100012352, name: Università degli Studi di Milano, award: PSR2015-1718, FABR2018
Language: English
Date published: 08/13/2019
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216602402771

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