Building multi-component crystals from cations and co-crystals: the use of chaperones

Bukenya, Shamim; Munshi, Tasnim; Scowen, Ian J.; Skyner, R.; Whitaker, Darren; Seaton, Colin C.

doi:10.1039/c2ce26498f

Cited by 13 publications

(7 citation statements)

References 40 publications

(8 reference statements)

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“…4-dimethylamino benzoic acid and the salt K + 3,5dinitrobenzoate is reported. 23 The third type of ionic co-crystal is the organic-inorganic aggregate between an organic molecule and an inorganic salt (whether constituted of monoatomic or polynuclear ions), viz. (nA)•M + X − .…”

Section: Oleksii Shemchukmentioning

confidence: 99%

Organic–inorganic ionic co-crystals: a new class of multipurpose compounds

2018

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Section: Oleksii Shemchukmentioning

confidence: 99%

Organic–inorganic ionic co-crystals: a new class of multipurpose compounds

2018

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“…[61][62][63] However, progress in making ICCs with three-or more molecular components is still lacking. [29,64] In the context of species comprising complex main group ionic species, such ICCs resemble the inverse coordination of salt lattices by metal phosphide complexes. .…”

Section: Direct Synthesis Of Ternary Cocrystal 2 (T2): (Se2p2n2)•(kbrmentioning

confidence: 99%

Direct and Telescopic Mechanochemical Synthesis of Higher-order Organic-Inorganic Hybrid Cocrystals: Tuning Order, Functionality and Size in Cocrystal Design

Ng¹,

Tan²,

Teo³

et al. 2021

Preprint

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The ability to rationally design and predictably construct crystalline solids has been the hallmark of crystal engineering research over the past two decades. When building higher-order multicomponent cocrystals (i.e. crystals containing more than two constituents), the differential and hierarchical way molecules interact and assemble in the solidstate is of pinnacle importance. To date, numerous examples of multicomponent crystals comprising organic molecules leading to salts, cocrystals or ionic cocrystals have been reported. However, the crystal engineering of hybrid organicinorganic cocrystals with sophisticated inorganic building blocks is still poorly understood and mostly unexplored. Here, we reveal the first efficient mechanochemical synthesis of higher-order hybrid organic-inorganic cocrystals based on the structurally versatile – yet largely unexplored – cyclodiphos(V/V)azane heterosynthon building block. The novel hybrid ternary and quaternary multicomponent cocrystals herein reported are held together by synergistic intermolecular interactions (e.g., hydrogen- and halogen-bonding, Se-π and ion-dipole interactions). Notably, higher-order ternary and quaternary cocrystals can be readily obtained either via direct synthetic routes from its individual components, or via unprecedented telescopic approaches from lower-order cocrystal sets. In addition, computational modelling has also revealed that the formation of higher-order cocrystals is thermodynamically driven, and that bulk moduli and compressibilities are strongly dependent on the chemical composition and intermolecular forces present in the crystals, which offer untapped potential for optimizing material properties.

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“…However, their salt forms or cocrystals are designed toward higher solubility that can overcome limited bioavailability problems (Brittain, 2013). Along with the prosperity of binary cocrystallization (Roy & Biradha, 2013), ternary or multicomponent cocrystallization is substantially more difficult, which was addressed by Aakerö y (Aakerö y et al, 2001), Nangia (Cherukuvada & Nangia, 2012), Desiraju (Chakraborty et al, 2014) and others (Aitipamula et al, 2013;Bukenya et al, 2013;Clarke et al, 2012;Chen et al, 2006) using strategies such as hydrogen bonding, halogen bonding or shape and size mimicry.…”

Section: Introductionmentioning

confidence: 99%

“…In the meantime, the combination of two or multiple APIs is very advantagous for better drug management, coping with drug resistance (Thakuria & Nangia, 2013;Shah et al, 2011;Chakraborty et al, 2014;Bukenya et al, 2013;Boardman et al, 2014). As the prototype structure of 5,5-substituted barbiturates, barbituric acid [2,4,6 (1H, 3H, 5H)-pyrimidinetrione] is a relatively weak organic acid in water (pK a = 4.03; Braga et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

From a binary salt to salt co-crystals of antibacterial agent lomefloxacin with improved solubility and bioavailability

Zhang

et al. 2015

Acta Crystallogr Sect B

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The cocrystallization of lomefloxacin (Lf) with barbituric acid (HBA) and/or isophthalic acid (H2ip) leads to novel binary and ternary salts via hydrogen-bonding recognition. X-ray single-crystal diffraction analyses show that zwitterionic lomefloxacin can adjust itself to fulfill a different supramolecular array in either binary salts or ternary salt co-crystals, formulated as [HLf]·[Hip]·H2O (1), [HLf]·[BA]·[HBA]·H2O (2) and [HLf]·[BA]·[H2ip]·CH3OH·H2O (3). These pharmaceutical agents present uniform charge-assisted hydrogen-bonding networks between HLf cations and acidic coformers with the lattice capturing water molecules. Structural comparison of (2) and (3) indicated that a delicate balance of geometries and hydrogen-bonding partners is required for stacking to favor the formation of ternary salt co-crystals. Cocrystallization was able to overcome the water insolubility of lomefloxacin. Both the salt co-crystals display enhanced solubility and better pharmaceutical applicability.

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Building multi-component crystals from cations and co-crystals: the use of chaperones

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Cited by 13 publications

References 40 publications

Organic–inorganic ionic co-crystals: a new class of multipurpose compounds

Organic–inorganic ionic co-crystals: a new class of multipurpose compounds

Direct and Telescopic Mechanochemical Synthesis of Higher-order Organic-Inorganic Hybrid Cocrystals: Tuning Order, Functionality and Size in Cocrystal Design

From a binary salt to salt co-crystals of antibacterial agent lomefloxacin with improved solubility and bioavailability

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