Synthesis of Anthradan analogues by regioselective Friedel–Crafts reactions on N,N-dihexylanthracen-2-amine

Miranda, Maicon G. de; Oliveira, Matheus F.G. de; Lopes, Rosângela S. C.; Silva, Antônio J. R. da; Albert, André Luís Mazzei; Lopes, Claudio C.

doi:10.1016/j.tetlet.2013.02.085

Cited by 3 publications

(1 citation statement)

References 17 publications

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“…Propargylamine, 4-(dimethylamino)pyridine (DMAP), p -toluenesulfonyl chloride (TsCl), sodium azide (NaN 3 ), triphosgene (BTC), deuterium oxide (D 2 O), tetramethylammonium (TMA) chloride, copper sulfate pentahydrate (CuSO 4 ·5H 2 O), and sodium ascorbic acid of analytical grade were obtained from Sigma-Aldrich Corp. and used as-received. 2-Amineanthracene was synthesized through the reduction of 2-aminoanthraquinone (Aladdin Industrial Co., Ltd.) according to the method in ref . Dichloromethane (DCM) and chloroform were obtained from Sigma-Aldrich Corp. and dried with 4A molecular sieve.…”

Section: Methodsmentioning

confidence: 99%

Preparation of a High-Strength Hydrogel with Slidable and Tunable Potential Functionalization Sites

Zheng

et al. 2015

Macromolecules

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A hydrogel with tunable potential functionalization sites has been successfully prepared. As potential functionalization sites, (2-hydroxypropyl)-α-CDs (Hy-α-CDs) were introduced into the network of tetrahedron-like poly(ethylene glycol) (tetra-PEG) gel through supramolecular chemistry. In the stage of complexation, poly-pseudo-rotaxane consisting of tetra-PEG macromonomer and Hy-α-CD formed in pregel solution. The dynamic complexation process and the structure of the poly-pseudo-rotaxane were investigated by NMR experiment. In the stage of gelation, some cross-linking reactions were completed through click chemistry. The structures and mechanical properties of the resultant hydrogels were characterized by ATR-FTIR, XPS, SEM, and compression test in detail. The number of Hy-α-CD introduced into the hydrogel is related closely to the structure of the poly-pseudo-rotaxane and can be controlled easily by tuning the feed ratio. Anthracene as an example of function was introduced into the hydrogel through Hy-α-CD to preliminarily demonstrate the validity of the potential functionalization site in the last, and the hydrogel also has the capacity for further diverse functionalization.

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Section: Methodsmentioning

confidence: 99%

Preparation of a High-Strength Hydrogel with Slidable and Tunable Potential Functionalization Sites

Zheng

et al. 2015

Macromolecules

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A Dipolar Anthracene Dye: Synthesis, Optical Properties and Two‐photon Tissue Imaging

Moon

Jun

Kim

et al. 2016

Chemistry An Asian Journal

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Two-photon microscopy is a powerful tool for studying biological systems. In search of novel two-photon absorbing dyes for bioimaging, we synthesized a new anthracene-based dipolar dye (anthradan) and evaluated its two-photon absorbing and imaging properties. The new anthradan, 9,10-bis(o-dimethoxy-phenyl)-anthradan, absorbs and emits at longer wavelengths than acedan, a well-known two-photon absorbing dye. It is also stable under two-photon excitation conditions and biocompatible, and thus used for two-photon imaging of mouse organ tissues to show bright, near-red fluorescence along with negligible autofluorescence. Such an anthradan thus holds promise as a new class of two-photon absorbing dyes for the development of fluorescent probes and tags for biological systems.

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Stereochemical Investigation of the Products of the Photoinduced Perfluoroalkylation–Dimerization of Anthracene

et al. 2015

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The photoinduced perfluoroalkylation of anthracene has been shown to provide 9,9',10,10'-tetrahydro-10,10'-diperfluoroalkyl-9,9'-bianthracenes in over 70% yields, each perfluoroalkyl iodide producing three diastereomers. The structures of all three diastereomers (cis,cis, cis,trans, and trans,trans isomers) have been elucidated by both NMR and X-ray crystallographic analyses. Most notably, an X-ray crystallographic analysis has revealed that the trans,trans diastereomer having the two trifluoromethyl groups in 10,10'-positions adopts a 74° twisted relationship of the two dihydroanthracene rings. Furthermore, each of the two trans,trans isomers 2a,b has been shown to exist as a mixture of new types of atropisomers and the energy barrier for the interconversion of the two atropisomers has been estimated to be 12 kcal/mol by variable-temperature NMR analysis.

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Synthesis of Anthradan analogues by regioselective Friedel–Crafts reactions on N,N-dihexylanthracen-2-amine

Cited by 3 publications

References 17 publications

Preparation of a High-Strength Hydrogel with Slidable and Tunable Potential Functionalization Sites

Preparation of a High-Strength Hydrogel with Slidable and Tunable Potential Functionalization Sites

A Dipolar Anthracene Dye: Synthesis, Optical Properties and Two‐photon Tissue Imaging

Stereochemical Investigation of the Products of the Photoinduced Perfluoroalkylation–Dimerization of Anthracene

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