Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

Tate, Daniel J.; Anemian, Rémi; Bushby, Richard J.; Nanan, Suwat; Warriner, S. L.; Whitaker, and Benjamin J

doi:10.3762/bjoc.8.14

Cited by 20 publications

(18 citation statements)

References 48 publications

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“…The tilted angle of the aromatic plane of ZnTNc exo in the stacks was estimated to be 16 degrees from the horizontal axis, based on the lattice parameters in the XRD analysis and the molecular dimensions from the DFT calculations. Liquid crystalline Pc and benzoporphyrins substituted with alkyl chains at the lateral positions also showed an eclipsed conformation with a tilt angle to the columnar axis . The lateral alkyl chains located at the crowded bay areas of ZnTNc exo reduce the strength of intermolecular interactions between the aromatic cores due to the steric repulsion of alkyl chains arranged out of the core plane.…”

Section: Resultsmentioning

confidence: 99%

Topological Control of Columnar Stacking Made of Liquid‐Crystalline Thiophene‐Fused Metallonaphthalocyanines

et al. 2015

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The spontaneous organization of two‐dimensional polyaromatic molecules into well‐defined nanostructures through noncovalent interactions is important in the development of organic‐based electronic and optoelectronic devices. Two regioisomers of thiophene‐fused zinc naphthalocyanines ZnTNcendo and ZnTNcexo have been designed and synthesized to obtain photo‐ and electroactive liquid crystalline materials. Both compounds exhibited liquid crystalline behavior over a wide temperature range through intermolecular π–π interactions and local phase segregation between the aromatic cores and peripheral side chains. The structural differences between ZnTNcendo and ZnTNcexo affected the stacking mode in self‐assembled columns, as well as symmetry of the two‐dimensional rectangular columnar lattice. The columnar structure in liquid crystalline phase exhibited an ambipolar charge‐transport behavior.

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Section: Resultsmentioning

confidence: 99%

Topological Control of Columnar Stacking Made of Liquid‐Crystalline Thiophene‐Fused Metallonaphthalocyanines

et al. 2015

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“…It is also one of the components in the synthesis of Zn-thio-Pc based dye sensitized solar cells and Zn-amide-Pc based photosensitizers [11]. Several researchers have synthesizedthe titlecompoundbyfollowing different synthetic procedures [9][10][11][12][13]. To the best of our knowledge, the title compound is only the second crystal structure to be reported in the family of dicyano-disulfonate compounds.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2,3-dicyano-1,4-phenylene bis(trifluoromethanesulfonate), C10H2F6N2O6S2

Tonder

Loganathan

Gohain

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The mixture was then chromatographed on silica gel with 100% n -pentane to afford the desired primary halides. This procedure was adopted from Tate et al 30 …”

Section: Methodsmentioning

confidence: 99%

Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium

Presley

Dalal

et al. 2017

Bioorganic & Medicinal Chemistry

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Antiplasmodial bioassay guided fractionation of a Madagascar collection of Crinum firmifolium led to the isolation of seven compounds. Five of the seven compounds were determined to be 2-alkylquinolin-4(1H)-ones with varying side chains. Compounds 1 and 4 were determined to be known compounds with reported antiplasmodial activities, while 5 was believed to be a new branched 2-alkylquinolin-4(1H)-one, however, it was isolated in limited quantities and in admixture and therefore was synthesized to confirm its structure as a new antiplasmodial compound. Along with 5, two other new and branched compounds 6 and 7 were synthesized as well. Accompanying the five quinolones were two known compounds 2 and 3 which are inactive against Plasmodium falciparum. The isolation, structure elucidation, total synthesis, and biological evaluation of these compounds are discussed in this article.

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Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

Cited by 20 publications

References 48 publications

Topological Control of Columnar Stacking Made of Liquid‐Crystalline Thiophene‐Fused Metallonaphthalocyanines

Topological Control of Columnar Stacking Made of Liquid‐Crystalline Thiophene‐Fused Metallonaphthalocyanines

Crystal structure of 2,3-dicyano-1,4-phenylene bis(trifluoromethanesulfonate), C10H2F6N2O6S2

Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium

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