Triphenylene hexa-n-alkylcyclohexanoates: a new series of disc-like liquid crystals

Beattie, David R.; Hindmarsh, Paul; Goodby, John W.; Haslam, S. D.; Richardson, Robert M.

doi:10.1039/jm9920201261

Cited by 21 publications

(8 citation statements)

References 7 publications

(2 reference statements)

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“…The acetate 14 was easily obtained in a quantitative yield when the reaction mixture of 8 and boron tribromide was treated with acetic anhydride before hydrolysis (Scheme 4). [19][20][21]…”

Section: Methodsmentioning

confidence: 99%

“…Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling 1841 HHTP) have been reported as novel materials having liquid crystalline properties 20. The newly synthesized octaacetoxytetraphenylene 14 should have some interesting properties.The zinc reagents reported here may have versatile applications for further development of chemistry.…”

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confidence: 99%

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Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Kabir

Iyoda

2000

Synthesis

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The intramolecular coupling of benzoannelated zincacyclopentadiene using CuCl 2 produced 1,8-dibromobiphenylene selectively in a good yield. On the contrary, the intermolecular coupling of zincacyclopentadiene produced 2,3,6,7,10,11,14,15-octamethoxytetraphenylene selectively in a synthetically reasonable yield under different reaction conditions. The reactions of 2,2¢-dilithio-4,4¢,5,5¢-tetramethoxybiphenyl and 2,2¢-dilithio-4,4¢,5,5¢-tetrakis(tert-butyldimethylsilyloxy)biphenyl with CuCl 2 in THF unexpectedly produced the corresponding tetraphenylene derivatives, instead of the desired biphenylene derivatives. Octamethoxytetraphenylene was used to synthesize octaacetoxytetraphenylene in a quantitative yield either directly or through octahydroxytetraphenylene.

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“…The acetate 14 was easily obtained in a quantitative yield when the reaction mixture of 8 and boron tribromide was treated with acetic anhydride before hydrolysis (Scheme 4). [19][20][21]…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Kabir

Iyoda

2000

Synthesis

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“…Scheme outlines the synthesis of the fused-core hexafunctional initiator and its use to prepare the fused-core six-arm star PMMA. The commercially available TP6OMe containing six methoxy groups attached to triphenylene were hydrolyzed to give TP6OH containing six hydroxyl functional groups . The ATRP initiating groups with −Br functionality were linked to each of the hydroxyl groups of TP6OH by an esterification reaction to form the hexafunctional fused-core initiator (TP6Br, named to indicate the linking structure between the ATRP initiating sites).…”

Section: Resultsmentioning

confidence: 99%

“…16 Synthesis of 2,3,6,7,10,11-Triphenylene Hexa-2-bromo-2-methylpropionate (TP6Br). TP6OMe was hydrolyzed into 2,3,6,7,10,11-hexahydroxytriphenylene (TP6OH) according to the literature method; 19 the product was recrystallized from deionized water and dried in a vacuum oven under N2. TP6OH (0.56 g, 1.7 mmol), anhydrous tetrahydrofuran (30 mL), and triethylamine (2.4 mL, 17 mmol) were charged into a dry 100 mL three-neck round-bottom reaction flask equipped with a stirring bar.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Direct Topology Visualization of High-Molecular-Weight Star PMMA

et al. 2005

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We report synthesis and direct topology visualization of single molecules of six-arm star poly(methyl methacrylate) (PMMA). We synthesized two hexafunctional initiators, 2,3,6,7,10,11-triphenylene hexa-2-bromo-2-methylpropionate (fused-core initiator) and ethylene glycol bis [3,4,5-tri(2-bromo-2-methylpropionate)] benzoylate (linear-core initiator). Their structures differ in the linking arrangement of the initiating sites. Atom transfer radical polymerizations (ATRP) of methyl methacrylate (MMA) from these initiators using CuCl as the catalyst and 4,4′-di-n-nonyl-2,2′-bipyridine as the ligand at 90 °C produced six-arm star PMMAs with very high molecular weight (M h w> 2 million) and narrow molecular weight distribution (polydispersity index ≈ 1.3). A high initiation efficiency (>90%) of the initiating sites is inferred from a good match of the M h w of the star PMMA with the expected value based on M h w of the cleaved arms. SEC-LS analysis confirmed the compact structure of the star PMMA compared to linear PMMA and the absence of star-star coupling. Tapping mode scanning force microscopy of a dip-coated sample on mica enabled resolution of the individual arms linked to the initiating core and allowed clear identification of predominantly six-arm star molecules.

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“…The starting materials, 3,5-dialkoxybenzoic acids [20] and 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) [13,18,[21][22][23], have been synthesised as reported previously. Symmetric benzoate esters of triphenylene have been synthesised by reacting an acid chloride with 2,3,6,7,10,11-hexahydroxytriphenylene in the presence of pyridine or triethylamine.…”

Section: Synthesismentioning

confidence: 99%

A columnar mesophase with high lateral order from a triphenylene-hexa(3,5-dialkoxy)benzoate

et al. 2010

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This paper describes the synthesis of triphenylene-2,3,6,7,10,11-hexayl hexakis(3,5-dialkoxy)benzoates, bearing hexyloxy (1a) and dodecyloxy tails (1b). These benzoate esters were synthesised in high yields by employing a DCC coupling of the (3,5-dialkoxy) benzoic acid to 2,3,6,7,10,11-hexahydroxytriphenylene. The 3,5-dihexyloxy benzoate 1a, forms a highly ordered columnar mesophase with extensive lateral and very limited columnar order, whereas no mesomorphic phases were observed for the 3,5-didodecyloxy benzoate 1b. In contrast with most benzoate esters of triphenylene, nematic mesophases were not observed for 1.

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Triphenylene hexa-n-alkylcyclohexanoates: a new series of disc-like liquid crystals

Cited by 21 publications

References 7 publications

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

Synthesis and Direct Topology Visualization of High-Molecular-Weight Star PMMA

A columnar mesophase with high lateral order from a triphenylene-hexa(3,5-dialkoxy)benzoate

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