Cocrystal Engineering of a High Nitrogen Energetic Material

Kent, Rosalyn V.; Wiscons, Ren A.; Sharon, Pessia; Grinstein, Dan; Frimer, Aryeh A.; Matzger, Adam J.

doi:10.1021/acs.cgd.7b01126

Cited by 77 publications

(64 citation statements)

References 24 publications

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“…Organic cocrystals are ordered solids assembled by intermolecular interactions, but cocrystallization only occurs between some certain molecules . That is, not all molecules can recognize and assemble to form a cocrystal.…”

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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“…Cocrystallization has proven to be an effective engineering strategy in many fields such as pharmaceuticals, energetics, and nonlinear optics . Through cocrystallization, novel materials with tailored properties can be generated from existing materials.…”

Section: Introductionmentioning

confidence: 99%

“…In the pharmaceutical cocrystal field, the electrostatic potentials of a ligand and its receptor can be used to screen the optimal ligand . Similarly, in the field of energetic cocrystals, the electrostatic potential maps were adopted by Kent's group to predict the behavior of the coformers with 3,6‐bis(1H‐1,2,3,4‐tetrazol‐5‐amino)‐1,2,4,5‐tetrazine (BTATz) and their obtained cocrystals exhibit good thermal stability and considerably low impact sensitivity . Therefore, the electrostatic potential surface can be utilized as a powerful tool to screen appropriate coformers for different energetic compounds.…”

Section: Introductionmentioning

confidence: 99%

Application of Molecular Electrostatic Potential Surface to Predict Supramolecular Synthons for RDX/Solvent Cocrystals

Wang

Zhao

Zhu

2019

Crystal Research and Technology

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Cocrystallization has attracted growing interests in the energetic field as it can tune properties by selecting and arranging existing molecules. Herein, the application of molecular electrostatic potential surface to predict supramolecular synthons for 1,3,5‐trinitro‐1,3,5‐triazinane (RDX)/solvent cocrystals is demonstrated. Six RDX/solvent supramolecular synthons are constructed and investigated by density functional theory. The results of Bader's atoms in molecules (AIM) and independent gradient model (IGM) indicate that unconventional CH···O type hydrogen bonds are the main intermolecular interactions between RDX and solvents. The thermodynamic properties are studied to assess the spontaneity of assembly reactions. The most stable packings for the supramolecular synthons of the RDX/solvents are predicted and they present lower sensitivity than RDX. The work may provide valuable insight for the rational design of RDX‐based cocrystals and promote the application of supramolecular chemistry in the field of explosives.

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“…In previous studies, the formation of multicomponent materials (solvates, and salts, ) from two energetic molecules has become an effective and easy method to tune the physical characteristics of energetic materials. Recently, co‐crystallization has emerged as an alternative approach to synthetic modification.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and Thermal Behavior of a Novel Insensitive Energetic Cocrystal Composed of 3,3′‐Bis(1,2,4‐oxadiazole)‐5,5′‐dione and 4‐Amino‐1,2,4‐triazole

Fei

Pang

2018

Zeitschrift anorg allge chemie

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A novel insensitive energetic cocrystal consisting of 3,3′‐bis(1,2,4‐oxadiazole)‐5,5′‐dione and 4‐amino‐1,2,4‐triazole in a 1:2 molar ratio was prepared and characterized. The structure of this cocrystal was characterized by single‐crystal X‐ray diffraction. The crystal structure of the cocrystal is a monoclinic system with P1 space group. Properties of the cocrystal studied included thermal decomposition and detonation performance. This cocrystal has a crystal density of 1.689 g·cm–3 at 173 K and good detonation performance (D = 6940 m·s–1, P = 20.9 GPa). Moreover, measured impact and friction sensitivities (IS > 40 J, FS > 360 N) show that it can be classified as an insensitive energetic material. Its thermodynamic properties indicate that it has moderate thermal stability with a sharp exothermic peak (244 °C, 5 K·min–1) and a high critical temperature of thermal explosion (523 K). In view of the observations above, it may serve as a promising alternative to known explosives such as TNT.

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Cocrystal Engineering of a High Nitrogen Energetic Material

Cited by 77 publications

References 24 publications

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Cocrystal Engineering: A Collaborative Strategy toward Functional Materials

Application of Molecular Electrostatic Potential Surface to Predict Supramolecular Synthons for RDX/Solvent Cocrystals

Synthesis, Crystal Structure, and Thermal Behavior of a Novel Insensitive Energetic Cocrystal Composed of 3,3′‐Bis(1,2,4‐oxadiazole)‐5,5′‐dione and 4‐Amino‐1,2,4‐triazole

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