Building co-crystals with molecular sense and supramolecular sensibility

Aakeröy, Christer B.; Salmon, Debra J.

doi:10.1039/b505883j

Cited by 701 publications

(479 citation statements)

References 106 publications

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“…The list of conformers was built based on composition of the cocrystals understood accordingly to the most common definition [9][10][11][12][13]. Hence, systems comprising components in liquid state under ambient conditions were excluded from the analysis, as well as ions, polymers, solvates (including hydrates) and clathrates.…”

Section: Computation Methods Training Sets Of Cocrystals and Coformersmentioning

confidence: 99%

“…This covers, among other domains, the pharmaceutical [3,4], agrochemical [5,6] or high-energy industries [6][7][8]. Not all multicomponent solids are classified as cocrystals [9] since at least two criterions must be met [9][10][11][12][13]. First of all, after cocrystallization, the molded homogeneous phase should comprise stoichiometric proportions of the components.…”

Section: Introductionmentioning

confidence: 99%

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Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Cysewski

2016

Struct Chem

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New virtual cocrystal screening was proposed taking advantage of the similarities between cocrystallization landscapes of different compounds. Assuming that cocrystallization propensities can be modeled by miscibility affinities of liquid components under supercooled conditions, the quantitative rules of likeness were formulated and validated for 45 aromatic and heteroaromatic amides interacting with a variety of coformers. The most important finding comes from the observed linear trends between the values of mixing enthalpies of amides with respect to a reference molecule. Particularly isonicotinamide was found as a very convenient comparative system since it constitutes 97 binary cocrystals. Many experimentally observed cocrystals were used for supporting the analogy hypothesis, which states that a properly selected reference molecule, for which cocrystals were experimentally documented, can provide practical information about cocrystallization propensities of another compound provided that two criterions are met, namely sufficiently high similarities and high enough affinities. Hence, it is not necessary to perform experimental cocrystallization of every pair of coformers since miscibility in the solid state of one compound can be transferred to another one at least in the case of aromatic or heteroaromatic amides.

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Section: Computation Methods Training Sets Of Cocrystals and Coformersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Cysewski

2016

Struct Chem

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“…There seems to be little scientific value in creating designations based on the state of one of the components under standard conditions, such as Aakeröy's suggestion that cocrystals should only be those composed of components that are solids at ambient temperature, 88 or based on whether the structure in question was found by accident or intent, as in the suggestion that cocrystals of current interest encompass an "element of design." 89 Similarly, recent suggestions that "pharmaceutical cocrystals" should be a subset of multicomponent crystals, similar to hydrates, solvates, clathrates, and inclusion crystals, 90 would perpetuate classifications based on some randomly selected property of one of the components (is it used as a solvent?…”

Section: How Common Is Polymorphism Among Organic Compounds? Current mentioning

confidence: 99%

Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Stahly

2007

Crystal Growth & Design

489

346

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A detailed description of polymorph screening procedures is presented. On the basis of the results of 245 polymorph screens, organic compounds were found to exist in multiple solid forms quite frequently. About 90% exhibited multiple crystalline and noncrystalline forms; about 50% exhibited polymorphism. Cocrystals are defined, and cocrystal screening is discussed. Data from 64 cocrystal screens show that cocrystals were found in 61% of the cases, and the total number of cocrystals found was 192.

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“…The non-covalent interactions such as hydrogen bonds and p-p stacking interactions have been considered the most powerful organizing elements in molecular self-assembly [8][9][10][11]. These forces between different moieties may result in the formation of multicomponent crystals, which are known as co-crystals [12]. The crystal structure analysis of the title compound revealed that it is a co-crystal of 10-bromo-9-phenylanthracene and anthracene-9,10-dione (ratio 2:1).…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 10-bromo-9-phenylanthracene–anthracene-9,10- dione (2:1), (C20H13Br)(C7H4O), C27H17BrO

Wang

2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was obtained as a by-product from the Suzuki coupling reaction of 9,10-dibromoanthracene and phenylboronic acid as described in literature [1]. Recrystallized from a dichloromethane/petroleum ether solution at room temperature yielded crystals suitable for single-crystal X-ray diffraction. DiscussionOrganic light emitting devices (OLEDs) have been attracting considerable attention due to their potential applications in flatpanel displays and solid-state lighting sources [1][2][3][4]. For the fullcolor OLEDs, highly efficient and stable three basic colors (red, green, and blue) emission are needed. However, it is difficult to produce a high-performance blue emission for its intrinsic characteristic of having a wide band gap irrespective of the type of material [5]. To obtain excellent colour purity, blue emitting materials should have molecular structures that can produce a broad and red-shifted electroluminescent emission [6]. 9,10-diphenylanthracene is a material well known for its high fluorescence quantum efficiency in diluted solution [7]. Recently, we have studied the Suzuki coupling reaction of 9,10-dibromoanthracene and phenylboronic acid and obtained the title compound as a by-product. The non-covalent interactions such as hydrogen bonds and p-p stacking interactions have been considered the most powerful organizing elements in molecular self-assembly [8][9][10][11]. These forces between different moieties may result in the formation of multicomponent crystals, which are known as co-crystals [12]. The crystal structure analysis of the title compound revealed that it is a co-crystal of 10-bromo-9-phenylanthracene and anthracene-9,10-dione (ratio 2:1). The phenyl ring is approximately perpendicular to anthracene ring (dihedral angles of 103.5°). In the title structur there are indications of a C-H···O hydrogen bond between the C=O group of the anthracene-9,10-dione and the adjacent C-H group of the phenyl ring (O···H: 2.55 Å) and p-p stacking interactions between the anthracene rings (interplane distances are about 3.923 Å and 3.978 Å). In addition, there also exist an intermolecular C-H···Br hydrogen bond between the Br atom and the adjacent C-H group of the phenyl ring (Br···H 2.896 Å), which link the molecules to a chain along the [110] direction.

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Building co-crystals with molecular sense and supramolecular sensibility

Cited by 701 publications

References 106 publications

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Diversity in Single- and Multiple-Component Crystals. The Search for and Prevalence of Polymorphs and Cocrystals

Crystal structure of 10-bromo-9-phenylanthracene–anthracene-9,10- dione (2:1), (C20H13Br)(C7H4O), C27H17BrO

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