Two novel violurate and squarate salts of cinchonine – Structures and physical properties

Koleva, Bojidarka B.; Bakalska, Rumyana; Seidel, Rüdiger W.; Kolev, Tsonko; Mayer‐Figge, Heike; Sheldrick, William S.; Spiteller, Michael

doi:10.1016/j.molstruc.2009.11.043

Cited by 5 publications

(3 citation statements)

References 31 publications

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“…All structures of organoammonium violurate salts are characterized by supramolecular self‐assembly through networks of N–H ··· N and N–H ··· O hydrogen bonds. In some cases, π–π stacking interactions between violurate anions has also been found . In aqueous solutions, alkali metal and organoammonium violurates display very similar violet colors with a λ max value in the range of 575–585 nm and an e value of ca.…”

Section: Introductionmentioning

confidence: 95%

“…This was followed by a detailed structural investigation of six new organoammonium salts (cyclohexylammonium, piperidinium, tetrahydroisoquinolinium, quinuclidinium, pyridinium, and 3‐aminopyridinium) by Sheldrick et al in 2009 . The same authors also reported the structures of ephedrinium and cinchoninium violurates , . All structures of organoammonium violurate salts are characterized by supramolecular self‐assembly through networks of N–H ··· N and N–H ··· O hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Structural Investigation of Brightly Colored Organoammonium Violurates

Liebing

Stein

Hilfert

et al. 2018

Zeitschrift anorg allge chemie

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Nine new organoammonium violurates [R 1 R 2 R 3 NH][C 4 H 2 N 3 O 4 ] [R 1 (4), R 3 = C 6 H 2 Me 2 -4,5-NH 2 -2 (5); R 1 = H, R 2 = R 3 = Et (6), iPr (7); R 1 = H, R 2 /R 3 = (-CH 2 -) 4 (8); R 1 = R 2 = R 3 = Et (9); R 1 = R 2 = Me, R 3 = (CH 2 ) 2 NMe 2 (10)] were prepared by treatment of violuric acid (1) with a variety of primary, secondary, and tertiary amines. With the exception of orange 5, all these violurate salts form bright blue or blue-purple crystalline solids. The acidic triethylammo-* Prof. Dr. F. T. Edelmann 36 nium violurate [NHEt 3 ]H[C 4 H 2 N 3 O 4 ] 2 ·H 2 O (9a) was isolated in the form of red-violet, plate-like crystals by the reaction of violuric acid hydrate with triethylamine in a molar ratio of 2:1 in ethanol. All compounds were fully characterized by their IR and NMR ( 1 H, 13 C) data as well as elemental analyses. X-ray crystal structures determinations of 2, 7, and 9a revealed supramolecular self-assembly through networks of N-H···N and N-H···O hydrogen bonds in the crystalline state.

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Investigation of Brightly Colored Organoammonium Violurates

Liebing

Stein

Hilfert

et al. 2018

Zeitschrift anorg allge chemie

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“…In multicomponent materials, the solid-state aggregation process can be more complex and chromophore dependent, thus it is often difficult to predict the interactions and to what extent they will impact the absorption. Despite the vast literature on chromic effects (Błasiak et al, 2017;Dzesse et al, 2018;Kolev et al, 2009;Koleva et al, 2010), there is no general recipe which would allow explanation of the origin of colour, as well as control the effect.…”

Section: Introductionmentioning

confidence: 99%

Origin of chromic effects and crystal-to-crystal phase transition in the polymorphs of tyraminium violurate

Gryl

Rydz

Wojnarska

et al. 2019

Int Union Crystallogr J

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Chromic materials are nowadays widely used in various technological applications, however understanding the effect and the possibility of tuning the obtained colour of a material are still challenging. Here a combined experimental and theoretical study is presented on the solvatochromic and crystallochromic effects in the (pseudo)polymorphs of tyraminium violurate. This organic material exhibits a large solvatochromic shift (ca 192 nm) associated with broad colour change (from yellow to dark violet). Tyraminum violurate crystallizes as red crystals of form (I) from water as a solvate, and as an unsolvated form [violet crystals of (II)] from methanol solution. Form (I), when heated, undergoes two crystal-to-crystal phase transformations associated with colour change of the crystals. Crystals of (II) show extreme birefringence (ca 0.46) and high refractive index (n γ above 1.90), which can be correlated with preferential orientation of the resultant dipole moments of the ions. Examination of optical effects (UV–Vis spectra) along with theoretical calculations (QTAIM, atomic and bond polarizabilities) enabled the description of the origin of colour in the studied materials.

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Review: the multicolored coordination chemistry of violurate anions

Lorenz

Liebing

Engelhardt

et al. 2019

Journal of Coordination Chemistry

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Two novel violurate and squarate salts of cinchonine – Structures and physical properties

Cited by 5 publications

References 31 publications

Synthesis and Structural Investigation of Brightly Colored Organoammonium Violurates

Synthesis and Structural Investigation of Brightly Colored Organoammonium Violurates

Origin of chromic effects and crystal-to-crystal phase transition in the polymorphs of tyraminium violurate

Review: the multicolored coordination chemistry of violurate anions

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