Supramolecular solids and time-resolved diffraction

Coppens, Philip; Zheng, Shao Liang; Gembický, Milan; Messerschmidt, Marc; Dominiak, Paulina M.

doi:10.1039/b610286g

Cited by 29 publications

(18 citation statements)

References 48 publications

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“…This article was first conceived as a chalk-and-blackboard talk delivered at the Indaba 5 conference "Models, Mysteries and Magic of Molecules" held at Berg-en-dal, Kruger National Park, South Africa (August [20][21][22][23][24][25]2006). …”

Section: Discussionmentioning

confidence: 99%

Crystal Engineering: A Holistic View

Desiraju¹

2007

Angew Chem Int Ed

1,333

866

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Crystal engineering, the design of molecular solids, is the synthesis of functional solid-state structures from neutral or ionic building blocks, using intermolecular interactions in the design strategy. Hydrogen bonds, coordination bonds, and other less directed interactions define substructural patterns, referred to in the literature as supramolecular synthons and secondary building units. Crystal engineering has considerable overlap with supramolecular chemistry, X-ray crystallography, materials science, and solid-state chemistry and yet it is a distinct discipline in itself. The subject goes beyond the traditional divisions of organic, inorganic, and physical chemistry, and this makes for a very eclectic blend of ideas and techniques. The purpose of this Review is to highlight some current challenges in this rapidly evolving subject. Among the topics discussed are the nature of intermolecular interactions and their role in crystal design, the sometimes diverging perceptions of the geometrical and chemical models for a molecular crystal, the relationship of these models to polymorphism, knowledge-based computational prediction of crystal structures, and efforts at mapping the pathway of the crystallization reaction.

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Section: Discussionmentioning

confidence: 99%

Crystal Engineering: A Holistic View

Desiraju¹

2007

Angew Chem Int Ed

1,333

866

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“…Z) isomerization of photoactive yellow protein (Rajagopal et al, 2004;Getzoff et al, 2003). As pointed out in recent publications (see, for example, Amirsakis et al, 2003;Toda & Bishop, 2004;Ananchenko et al, 2006;Halder & Kepert, 2006;Zouev et al, 2006;Coppens et al, 2006), supramolecular host-guest solids dramatically increase the possibility of monitoring photochemically induced processes in the periodic solid state. By embedding photoactive species in an inert host lattice, three-dimensional periodicity can often be retained as a reaction proceeds.…”

Section: Introductionmentioning

confidence: 96%

Single-crystal-to-single-crystal E → Z isomerization of tiglic acid in a supramolecular framework

Zheng

Messerschmidt

Coppens

2007

Acta Crystallogr Sect B

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The single-crystal-to-single-crystal E --> Z photoisomerization of tiglic acid (2,3-dimethylacrylic acid) occurs in the supramolecular crystals CECR-HTA x 2MeOH x 1.5H(2)O (1) (where HTA = tiglic acid, CECR = C-ethylcalix[4]resorcinarene) with the preservation of the crystal lattice, indicating the ;scaffolding effect' of the molecular framework, which holds the crystal together notwithstanding the change in shape of the embedded guest molecules. A photostationary state is reached at a concentration of ca 30% of the Z isomers. A kinetic analysis shows the Z --> E back-reaction to proceed with a larger rate constant than the E --> Z isomerization.

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“…As an aside, the study of guests enclatherated in host networks is not novel and was performed over two decades ago where guest molecules were cocrystallized within porphyrin networks, and it is of interest to note that the authors explicitly call these systems 'sponges' within the article's title (Byrn et al, 1993). Fujita and co-workers subsequently described a variant of the solid-state dilution method (Coppens et al, 2006(Coppens et al, , 2008Coppens & Zheng, 2011) to study the mechanism of Pdcatalyzed aromatic bromination using a substrate that was enclatherated within the sponge during crystal growth (Ikemoto et al, 2014), in a manner resembling the X-ray crystallographic studies of the ultraviolet-light-induced formation and proposed observation of 1,3-dimethylcyclobutadiene in a guanidinium sulfonate-calixarene crystalline network with reaction intermediate monitoring (Legrand et al, 2010a,b;Alabugin et al, 2010;Scheschkewitz, 2010). However, as time progressed, it became evident that data quality was an issue for this method and eventually a correction for the original report was published that pertained to the incorrect stereochemical determination of miyakosyne A (Inokuma et al, 2013b).…”

Section: Introductionmentioning

confidence: 99%

Analysis of rapidly synthesized guest-filled porous complexes with synchrotron radiation: practical guidelines for the crystalline sponge method

et al. 2015

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This report describes complete practical guidelines and insights for the crystalline sponge method, which have been derived through the first use of synchrotron radiation on these systems, and includes a procedure for faster synthesis of the sponges. These guidelines will be applicable to crystal sponge data collected at synchrotrons or in-house facilities, and will allow researchers to obtain reliable high-quality data and construct chemically and physically sensible models for guest structural determination.

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Supramolecular solids and time-resolved diffraction

Cited by 29 publications

References 48 publications

Crystal Engineering: A Holistic View

Crystal Engineering: A Holistic View

Single-crystal-to-single-crystal E → Z isomerization of tiglic acid in a supramolecular framework

Analysis of rapidly synthesized guest-filled porous complexes with synchrotron radiation: practical guidelines for the crystalline sponge method

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