The Role of Cocrystals in Solid-State Synthesis:  Cocrystal-Controlled Solid-State Synthesis of Imides

Cheney, Miranda L.; McManus, Gregory J.; Perman, Jason A.; Wang, and Zhenqiang; Zaworotko, Michael J.

doi:10.1021/cg0701729

Cited by 76 publications

(54 citation statements)

References 18 publications

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“…Most recently, in the field of pharmaceuticals, co-crystallization has been shown to be an effective means of altering a drug's physical properties, such as solubility and melting point [152][153][154]. Several of these are pharmaceutically acceptable co-crystals, including 1:1 complexes of caffeine with antibiotic sulfa drugs [155][156][157].…”

Section: Importance Of Co-crystalmentioning

confidence: 99%

Molecular recognition of caffeine in solution and solid state

Sahoo

2015

Bioorganic Chemistry

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Section: Importance Of Co-crystalmentioning

confidence: 99%

Molecular recognition of caffeine in solution and solid state

Sahoo

2015

Bioorganic Chemistry

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“…An archetypal example of such a system is the compound ROY, which produces a wide variety of polymorphs with colors ranging from red to orange and yellow . Even greater diversity may be achieved by producing multicomponent cocrystals in which coformer molecules electronically interact with the organic chromophore, often causing large changes in the band gap and, therefore, color . Furthermore, the use of cocrystals in optical materials is not limited to the modification of color: recent work in our group has shown that cocrystallization is also a successful method for modifying the luminescent properties of organic compounds …”

Section: Introductionmentioning

confidence: 99%

Rationalization of the Color Properties of Fluorescein in the Solid State: A Combined Computational and Experimental Study

Arhangelskis

Eddleston

Reid

et al. 2016

Chemistry A European J

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Fluorescein is known to exist in three tautomeric forms defined as quinoid, zwitterionic, and lactoid. In the solid state, the quinoid and zwitterionic forms give rise to red and yellow materials, respectively. The lactoid form has not been crystallized pure, although its cocrystal and solvate forms exhibit colors ranging from yellow to green. An explanation for the observed colors of the crystals is found using a combination of UV/Vis spectroscopy and plane‐wave DFT calculations. The role of cocrystal coformers in modifying crystal color is also established. Several new crystal structures are determined using a combination of X‐ray and electron diffraction, solid‐state NMR spectroscopy, and crystal structure prediction (CSP). The protocol presented herein may be used to predict color properties of materials prior to their synthesis.

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“…9 Potember and his group in 1982 suggested the optical memory effect of the metal-TCNQ charge transfer complex. 13,14 Solid-state synthesis is a rapidly emerging field in synthetic chemistry not only in organic synthesis scenarios [15][16][17] but also in co-crystal chemistry. 11 These results underline the importance of understanding the features of solid-state reactivity to predict the properties of the final device.…”

Section: Introductionmentioning

confidence: 99%

Rational design of the solid-state synthesis of materials based on poly-aromatic molecular complexes

et al. 2016

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The possibility of exploiting a thermally-induced solid-state reaction to obtain the formation of a fluorene and TCNQ molecular complex was proposed by some of us (Kumar et al. Crystal Growth & Design, 2009, 9(8), 3396-3404). In this paper, we generalize and rationalize the approach to other charge transfer (CT) molecular complexes with naphthalene and anthracene, changing the size of the donor moiety to propose a general approach for the preparation of this class of materials by exploiting the solid-state synthesis method. Moreover, the kinetic features of the solid state reactions were fully elucidated by Raman spectroscopy and High Resolution X-ray Powder Diffraction analysis (in situ Raman/XRPD), exploiting the Avrami equation in isothermal and non-isothermal conditions, rate constants, reaction orders and activation energies were obtained. All the three tested solid-state charge transfer (SS-CT) reactions resulted to obey a general rule, whereby predicting the most apt reaction temperature. Finally, a method based on principal component analysis (PCA) for a fast kinetic analysis of in situ XRD synchrotron data was successfully developed, employing a formalism suitable for the analysis of non-isothermal reaction data, thus allowing a high throughput approach for the fast screening of the kinetics of parent reactions. PCA analysis was exploited as an alternative technique to obtain kinetic information in a faster and more efficient way, which can be used for on line monitoring and/or in all those cases where Rietveld analysis is not feasible. Figure 4 Initial (a) and final (b) Raman spectra for NA-TCNQ formation reaction and variation of the Raman peak of TCNQ at 1600 cm -1 within time (c). Reaction coordinates and kinetic analysis (Kennedy and Clark approach) of Raman data for NA-TCNQ (d and e) and FL-TCNQ (f and g). Linear fit of NA-TCNQ (b): Equation y=-8421 (1438)*x+20(4) Rsq. = 0.847. Ea = 70kJ/mol. Linear fit of FL-TCNQ (d): Equation y=-21443 (3562)*x+55(10.) Rsq. = 0.854. Ea = 178kJ/mol

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The Role of Cocrystals in Solid-State Synthesis: Cocrystal-Controlled Solid-State Synthesis of Imides

Abstract: Cocrystal-controlled solid-state synthesis (C 3 S 3 ) of imides occurs via heating of cocrystals formed between anhydride and aromatic amine cocrystal formers.

Cited by 76 publications

References 18 publications

Molecular recognition of caffeine in solution and solid state

Molecular recognition of caffeine in solution and solid state

Rationalization of the Color Properties of Fluorescein in the Solid State: A Combined Computational and Experimental Study

Rational design of the solid-state synthesis of materials based on poly-aromatic molecular complexes

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