@article {46400, title = {Design and synthesis of 3D porous diamondoid frameworks by cocrystallization}, journal = {Acta Crystallographica A-Foundation and Advances}, volume = {70}, year = {2014}, month = {MAY}, pages = {C470}, type = {Meeting Abstract}, keywords = {cocrystals, crystal engineering, Porous Organic Cages}, issn = {2053-2733}, author = {Tothadi, Srinu and Little, Marc A. and Hasell, Tom and Briggs, Michel E. and Chong, Samantha Y. and Cooper, Andrew I.} } @article { ISI:000340469800024, title = {Highly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions}, journal = {Chemistry-A European Journal}, volume = {20}, number = {33}, year = {2014}, month = {AUG}, pages = {10343-10350}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

An excellent chiral symmetry-breaking spontaneous enantiomeric resolution phenomenon, denoted preferential enrichment, was observed on recrystallization of the 1:1 cocrystal of dl-arginine and fumaric acid, which is classified as a racemic compound crystal with a high eutectic ee value (\>95\%), under non-equilibrium crystallization conditions. On the basis of temperature-controlled video microscopy and in situ time-resolved solid-state (CNMR)-C-13 spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed.

}, keywords = {Amino acids, chiral resolution, cocrystals, Crystal growth, phase transitions}, issn = {0947-6539}, doi = {10.1002/chem.201402446}, author = {Iwama, Sekai and Kuyama, Kazunori and Mori, Yuko and Manoj, Kochunnoonny and Gonnade, Rajesh G. and Suzuki, Katsuaki and Hughes, Colan E. and Williams, P. Andrew and Harris, Kenneth D. M. and Veesler, Stephane and Takahashi, Hiroki and Tsue, Hirohito and Tamura, Rui} } @article {46393, title = {Pharmaceutical solids in crystal engineering}, journal = {Acta Crystallographica A-Foundation and Advances}, volume = {70}, year = {2014}, month = {MAY}, pages = {C12}, type = {Meeting Abstract}, keywords = {cocrystals, crystal engineering, Supramolecular synthon}, issn = {2053-2733}, author = {Nangia, Ashwini} } @article { ISI:000368141200024, title = {Drug-drug molecular salt hydrate of an anticancer drug gefitinib and a loop diuretic drug furosemide: an alternative for multidrug treatment}, journal = {Journal of Pharmaceutical Sciences}, volume = {104}, number = {12}, year = {2015}, month = {DEC}, pages = {4207-4216}, publisher = {WILEY-BLACKWELL}, address = {111 RIVER ST, HOBOKEN 07030-5774, NJ USA}, abstract = {

A 1:1 monohydrate salt containing gefitinib, an orally administrated chemotherapy treatment for lung and breast cancers and furosemide, a loop diuretic drug, commonly used in the treatment of hypertension and edema, has been prepared. The molecular salt crystallized in triclinic P-1 space group. The CO bond lengths (similar to 1.26 angstrom) in the COOH group show that proton transfer has occurred from furosemide to morpholine moiety of the gefitinib suggesting cocrystal to be ionic. The morpholine moiety of the gefitinib showed significant conformational change because of its involvement in conformation dictating the strong N-H center dot center dot center dot O hydrogen bonding interaction. The strong hydrogen bonding interaction between gefitinib and furosemide places their benzene rings in stacking mode to facilitate the generation of pi-stack dimers. The neighboring dimers are bridged to each other via water molecule through N-H center dot center dot center dot O, C-H center dot center dot center dot O, O-H center dot center dot center dot N, and O-H center dot center dot center dot O interactions. The remarkable stability of the salt hydrate could be attributed to the strong hydrogen bonding interactions in the crystal structure. Interestingly, release of water from the lattice at 140 degrees C produced new anhydrous salt that has better solubility and dissolution rate than salt hydrate. The drug-drug molecular salt may have some bearing on the treatment of patient suffering from anticancer and hypertension. (C) 2015 Wiley Periodicals, Inc. and the American Pharmacists Association

}, keywords = {cancer chemotherapy, cocrystals, crystal engineering, crystal structure, dissolution rate, hydrate, phase transition, solubility, stability, thermal analysis}, issn = {0022-3549}, doi = {10.1002/jps.24651}, author = {Thorat, Shridhar H. and Sahu, Sanjay Kumar and Patwadkar, Manjusha V. and Badiger, Manohar V. and Gonnade, Rajesh G.} } @article {43908, title = {Modular assembly of porous organic cage crystals: isoreticular quasiracemates and ternary co-crystal}, journal = {CrystEngComm}, volume = {19}, year = {2017}, month = {SEP}, chapter = {4933-4941}, abstract = {

Small changes in molecular structure and crystallisation conditions can have a profound effect on the crystal packing of molecules. Increasing the system complexity-for example, by introducing multiple components-greatly increases the number of potential outcomes. Hence, the rational design of porous cocrystals with multiple components is challenging. Here, we report a family of isoreticular quasiracemate crystalline phases for porous organic cages, FT-RCC3-R center dot CCX-S (where X = 1, 2, or 4), that were prepared in a modular and predictable fashion. By using directional intermolecular interactions between cages, we were able to prepare a rare ternary co-crystal, (CC3-S(0.5)CC4-S-0.5)center dot(CC13-S(0.5)CC3-S(0.25)CC4-S-0.25).

}, keywords = {cocrystals, Frameworks, Gas-chromatography, Halogen Bonds, Hydrogen-bonds, Molecular Cage, Nanoparticles, Pores, porosity, Separation}, issn = {1466-8033}, doi = {10.1039/c7ce00783c}, author = {Tothadi, Srinu and Little, Marc A and Hasell, Tom and Briggs, Michael E. and Chong, Samantha Y. and Liu, Ming and Cooper, Andrew I.} } @article {46069, title = {Supramolecular synthon hierarchy in sulfonamide cocrystals with syn-amides and N-oxides}, journal = {IUCRJ}, volume = {6}, year = {2019}, month = {JUL}, pages = {751-760}, type = {Article}, abstract = {

Sulfonamide drugs are well known antibacterial and antimicrobial molecules for pharmaceutical development. Building a library of suitable supramolecular synthons for the sulfonamide functional group and understanding their crystal structures with partner coformer molecules continues to be a challenge in crystal engineering. Although a few sulfonamide cocrystals with amides and N-oxides have been reported, the body of work on sulfonamide synthons is limited compared with those that have carboxylic acids and carboxamides. To address this structural gap, the present work is primarily focused on sulfonamide-lactam and sulfonamide-syn-amide synthons with drugs such as celecoxib, hydrochlorothiazide and furosemide. Furthermore, the electrostatic potential of previously reported cocrystals has been recalculated to show that the negative electrostatic potential on the lactam and syn-amide O atom is higher compared with the charge on carboxamide and pyridine N-oxide O atoms. The potential of sulfonamide molecules to form cocrystals with syn-amides and lactams are evaluated in terms of the electrostatic potential energy for the designed supramolecular synthons.

}, keywords = {cocrystals, crystal engineering, sulfonamides, supramolecular synthons, syn-amides}, issn = {2052-2525}, doi = {10.1107/S2052252519005037}, author = {Bolla, Geetha and Nangia, Ashwini} } @article {47667, title = {Crystal structure analysis of highly efficient chiral resolution of (RS)-arginine-fumaric acid cocrystal under preferential enrichment conditions}, journal = {Journal of Molecular Structure}, volume = {1245}, year = {2021}, month = {DEC }, pages = {131073}, type = {Article}, abstract = {Two new hydrate cocrystals, (RS)-arginine-fumaric acid-H2O ( 2 ) and (S)-arginine-2 fumaric acid-H2O ( 3 ), were obtained by the slow evaporation of the saturated aqueous ethanol solution of a 1:1 mixture of S-enriched arginine (33\% ee) and fumaric acid or (S)-arginine and fumaric acid, respectively. Cocrystals 2 and 3 possess an isostructural molecular organization containing homochiral 1D chains of arginine sim-ilar to that of the anhydrous cocrystal of (RS)-arginine-fumaric acid ( 1 ). The latter showed an efficient {\textquoteleft}{\textquoteleft}preferential enrichment (PE){\textquoteright}{\textquoteright}, a unique spontaneous enantiomeric resolution phenomenon by simple recrystallization from the highly supersaturated solution. The formation of unstable cocrystals 2 and 3 seems to have played a crucial role in the enrichment of arginine in the mother liquor under PE crystal-lization conditions. (c) 2021 Elsevier B.V. All rights reserved.}, keywords = {Arginine, cocrystals, crystal structure, Enantiomeric resolution, preferential enrichment}, issn = {0022-2860}, doi = {10.1016/j.molstruc.2021.131073}, author = {Manoj, Kochunnoonny and Takahashi, Hiroki and Iwama, Sekai and Gonnade, G. Rajesh and Tsue, Hirohito and Tamura, Rui} } @article {49069, title = {Highly electrostrictive salt cocrystal and the piezoelectric nanogenerator application of its 3D-printed polymer composite}, journal = {ACS Applied Materials and Interfaces }, volume = {16}, year = {2024}, month = {MAY}, pages = {26406-26416}, type = {Article}, abstract = {

Ionic cocrystals with hydrogen bonding can form exciting materials with enhanced optical and electronic properties. We present a highly moisture-stable ammonium salt cocrystal [CH3C6H4CH(CH3)NH2][CH3C6H4CH(CH3)NH3][PF6] ((p-TEA)(p-TEAH)PF6) crystallizing in the polar monoclinic C2 space group. The asymmetry in (p-TEA)(p-TEAH)PF6 was induced by its chiral substituents, while the polar order and structural stability were achieved by using the octahedral PF6- anion and the consequent formation of salt cocrystal. The ferroelectric properties of (p-TEA)(p-TEAH)PF6 were confirmed through P-E loop measurements. Piezoresponse force microscopy (PFM) enabled the visualization of its domain structure with characteristic {\textquoteleft}{\textquoteleft}butterfly{\textquoteright}{\textquoteright} and hysteresis loops associated with ferro- and piezoelectric properties. Notably, (p-TEA)(p-TEAH)PF6 exhibits a large electrostrictive coefficient (Q(33)) value of 2.02 m(4) C-2, higher than those found for ceramic-based materials and comparable to that of polyvinylidene difluoride. Furthermore, the composite films of (p-TEA)(p-TEAH)PF6 with polycaprolactone (PCL) polymer and its gyroid-shaped 3D-printed composite scaled-up device, 3DP-Gy, were prepared and evaluated for piezoelectric energy-harvesting functionality. A high output voltage of 22.8 V and a power density of 118.5 mu W cm(-3) have been recorded for the 3DP-Gy device. Remarkably, no loss in voltage outputs was observed for the (p-TEA)(p-TEAH)PF6 devices even after exposure to 99\% relative humidity, showcasing their utility under extremely humid conditions.

}, keywords = {3D printing, cocrystals, energy harvesting, ferroelectricity, Piezoelectricity}, issn = {1944-8244}, doi = {10.1021/acsami.4c03349}, author = {Sahoo, Supriya and Panday, Rishukumar and Kothavade, Premkumar and Sharma, Vijay Bhan and Sowmiyanarayanan, Anirudh and Praveenkumar, Balu and Zareba, Jan K. and Kabra, Dinesh and Shanmuganathan, Kadhiravan and Boomishankar, Ramamoorthy} }