Absorption of hydrogen bond donors by pyridyl bis -urea crystals

Kinkini Roy; Arief C. Wibowo; Perry J. Pellechia; Shuguo Ma; Michael F. Geer; Linda S. Shimizu

doi:10.1021/cm302658q

Absorption of hydrogen bond donors by pyridyl bis -urea crystals

Kinkini Roy, Arief C. Wibowo, Perry J. Pellechia, Shuguo Ma, Michael F. Geer, Linda S. Shimizu

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

9 Citations (Scopus)

Abstract

A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.

Original language	English
Pages (from-to)	4773-4781
Number of pages	9
Journal	Chemistry of Materials
Volume	24
Issue number	24
DOIs	https://doi.org/10.1021/cm302658q
Publication status	Published - 21 Dec 2012
Externally published	Yes

Keywords

guest absorption
porous crystals
solid-to-solid transformation
ureas

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10.1021/cm302658q

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abstract = "A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.",

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T1 - Absorption of hydrogen bond donors by pyridyl bis -urea crystals

AU - Roy, Kinkini

AU - Wibowo, Arief C.

AU - Pellechia, Perry J.

AU - Ma, Shuguo

AU - Geer, Michael F.

AU - Shimizu, Linda S.

PY - 2012/12/21

Y1 - 2012/12/21

N2 - A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.

AB - A one-dimensional crystalline solid built from pillars of self-assembled bis-urea pyridyl macrocycles affords a close packed structure with no pores. These organic pillars contain unsatisfied urea oxygen lone pairs that can be used to drive the absorption of alcohols including trifluoroethanol, phenol, pentafluorophenol, and ethylene glycol to give well-ordered host:guest complexes with repeatable stoichiometry. The driving force for reversible solid transitions appears to be the formation of hydrogen bonds between the guest and an unsatisfied hydrogen bond acceptor, which is a lone pair of the urea oxygen. Halogen bonding with the electrophilic iodide in pentafluoroiodobenzene can also drive absorption by the host to give a well-ordered host:guest complex. These results suggest that the organic solid-state is surprisingly dynamic and may have potential applications for sorbents.

KW - guest absorption

KW - porous crystals

KW - solid-to-solid transformation

KW - ureas

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Absorption of hydrogen bond donors by pyridyl bis -urea crystals

Abstract

Keywords

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