Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Topić, Filip; Rissanen, Kari

doi:10.1021/jacs.6b02854

Cited by 114 publications

(113 citation statements)

References 42 publications

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“…The bond strength is shown to be energetically competitive and sometimes stronger than the hydrogen bond, which increases with the increase size of the halogen donor atom, that is, F < Cl < Br < I. With superior strength and directionality, the halogen bond would also promote the construction of robust and reproducible cocrystal structures . Extensive functional groups could engage in the recognition and coassembly processes, wherein plenty of electron‐rich species have been explored as halogen‐bond acceptors, i.e., π systems, N‐, S‐, or Se‐based acceptors .…”

Section: Rational Design and Controllable Preparation Of Organic Cocrmentioning

confidence: 99%

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

et al. 2019

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materials, [9][10][11][12] which are crystalline singlephase materials composed of two or more different compounds generally in a stoichiometric ratio, [13] providing a platform for unveiling the structure-property relationships at a molecular level. [14] The building blocks are assembled via noncovalent interactions, offering the opportunity to achieve noncovalent synthesis of functional molecules. [15] Compared with the traditional covalent synthesis, cocrystal engineering offers numerous advantages, including: 1) avoiding complicated synthesis procedures, and cocrystal assemblies have been successfully fabricated by the vapor methods and solution-processing methods in a facile and low-cost way; 2) manipulating intermolecular interactions through selecting suitable conformers from a plentiful supply of raw materials, resulting in tunable structures, morphologies, and sizes; 3) achieving rare and multifunctional properties through a collaborative strategy in distinct constituent units, which are difficult to realize for individual components. [16][17][18] Cocrystal engineering began to draw much attention since the exploration of the metal conductive tetrathiafulvalene-7,7,8,8-tetracyanoquinodimethane (TTF-TCNQ) cocrystals in 1973. [19] The peculiar conductivity in organic materials makes it possible for cocrystals to serve as organic electrodes, which can effectively lower the contact resistance and further improve device performance. Encouraged by this, cocrystals can serve as a breakthrough and provide an opportunity to discover novel physicochemical properties, which are far beyond the performance of single materials. In this respect, dielectric response [20] and nonlinear optics [21,22] are also realized through rational design of each component, which is absent in their constitute components. Even more, the bottom-up supramolecular assembly provides the opportunity to equip them with the individual properties of the donor or acceptor to create multifunctional materials. [23] Typically, ambipolar charge transport can be generated by coassembling p-type semiconductors and n-type ones, and the charge-carrier mobility is now up to 1.57 cm 2 V −1 s −1 for holes and 0.47 cm 2 V −1 s −1 for electrons. [24] To date, these exciting results accelerate the investigations of organic functional cocrystals, such as room-temperature ferroelectricity, [25][26][27] optical waveguide properties, [28,29] pure organic room-temperature phosphorescent properties, [30][31][32] stimulusresponse (e.g., mechanical stress, [33,34] heat, [35,36] or solvent [37] ) characteristics, photovoltaics, [38] and near-infrared photothermal (PT) conversion and imaging, [39] etc.Cocrystal engineering with a noncovalent assembly feature by simple constituent units has inspired great interest and has emerged as an efficient and versatile route to construct functional materials, especially for the fabrication of novel and multifunctional materials, due to the collaborative strategy in the distinct constituent units. Meanwhile, the precise crystal a...

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Section: Rational Design and Controllable Preparation Of Organic Cocrmentioning

confidence: 99%

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

et al. 2019

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“…This method has great potential in the synthesis of multicomponent co-crystals based on polytopic co-formers. Thus, H-bonded heterosynthons are able to interact with the third co-former through halogen bonds [226][227][228]. π-Stacking in conjunction with hydrogen bonding was used for synthesis of ternary co-crystals [229,230].…”

Section: Co-crystals Designmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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“…moieties is their use as the building block base in the synthesis of crown ethers . This type of molecule discovered by Pedersen in 1967 was the starting point for the fields of supramolecular and biomimetic chemistry .…”

Section: Introductionmentioning

confidence: 99%

Cu⁺‐catalyzed 1,3‐Dipolar Intramolecular Click Opposite Cross Cyclization Reaction of Polyoxyethylene Bis(azido‐terminal alkynes): Synthesis of New 1,2,3‐Triazolo‐crown Ethers

Mekni

2017

Journal of Heterocyclic Chem

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Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Cited by 114 publications

References 42 publications

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Cu⁺‐catalyzed 1,3‐Dipolar Intramolecular Click Opposite Cross Cyclization Reaction of Polyoxyethylene Bis(azido‐terminal alkynes): Synthesis of New 1,2,3‐Triazolo‐crown Ethers

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Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Cited by 114 publications

References 42 publications

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Cu+‐catalyzed 1,3‐Dipolar Intramolecular Click Opposite Cross Cyclization Reaction of Polyoxyethylene Bis(azido‐terminal alkynes): Synthesis of New 1,2,3‐Triazolo‐crown Ethers

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Cu⁺‐catalyzed 1,3‐Dipolar Intramolecular Click Opposite Cross Cyclization Reaction of Polyoxyethylene Bis(azido‐terminal alkynes): Synthesis of New 1,2,3‐Triazolo‐crown Ethers