- Synthesis of sterically crowded 9-nitrotriptycenes by the Diels–Alder cycloaddition reaction
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The synthesis of novel sterically crowded triptycenes as attractive components for the construction of models for various molecular dynamic studies is reported. 9-Nitrotriptycenes were obtained by the Diels–Alder reactions between 9-nitroanthracene and tetrabromobenzyne as well as 1,4-dichloro-9-nitroanthracene and 2,6-dichlorobenzyne. Interesting regioselectivity relative to the central and terminal rings was observed. Moreover, 1,2,3,4-tetrabromo-9-nitrotriptycene was further functionalized to afford 1,2,3,4-tetrabromotriptycyl-9-ammonium tetrafluoroborate in two-steps. The impact of steric hindrance on the geometry of the molecule was estimated on the basis of single crystal X-ray diffraction data.
- Szupiluk, Artur
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p. 5251 - 5253
(2016/11/13)
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- The electrochemistry of arylated anthraquinones in room temperature ionic liquids
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Arylated anthraquinone derivatives of different sizes and different π-basicities have been prepared, and the electrochemical behaviour of these substances has been studied on screen printed graphite electrodes in the three room temperature ionic liquids (RTILs), 1-butyl-3-methylimidazolium hexafluorophosphate ([C4MIM][PF6]), 1-hexyl-3- methylimidazolium hexafluorophosphate ([C6MIM][PF6]) and 1-octyl-3-methylimidazolium hexafluorophosphate ([C8MIM][PF 6]). Half redox potentials for the first and second one electron reduction waves were identified, and the diffusion coefficient values were estimated from cyclic voltammetry measurements. The influence of the nature of the RTIL and of the substitution pattern of the anthraquinone on the solvodynamic radii were studied. A correlation of the reductive potentials with the corresponding Hammett constants of the substituents was tested. Copyright
- Gomis-Berenguer, Alicia,Gomez-Mingot, Maria,Garcia-Cruz, Leticia,Thiemann, Thies,Banks, Craig E.,Montiel, Vicente,Iniesta, Jesus
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p. 367 - 375
(2013/05/21)
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- Polymerization of novel methacrylated anthraquinone dyes
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A new series of polymerizable methacrylated anthraquinone dyes has been synthesized by nucleophilic aromatic substitution reactions and subsequent methacrylation. Thereby, green 5,8-bis(4-(2-methacryloxyethyl)phenylamino)-1,4- dihydroxyanthraquinone (2), blue 1,4-bis(4-((2-methacryloxyethyl)oxy) phenylamino)anthraquinone (6) and red 1-((2-methacryloxy-1,1- dimethylethyl)amino)anthraquinone (12), as well as 1-((1,3-dimethacryloxy-2- methylpropan-2-yl)amino)anthraquinone (15) were obtained. By mixing of these brilliant dyes in different ratios and concentrations, a broad color spectrum can be generated. After methacrylation, the monomeric dyes can be covalently emplaced into several copolymers. Due to two polymerizable functionalities, they can act as cross-linking agents. Thus, diffusion out of the polymer can be avoided, which increases the physiological compatibility and makes the dyes promising compounds for medical applications, such as iris implants.
- Dollendorf, Christian,Kreth, Susanne Katharina,Choi, Soo Whan,Ritter, Helmut
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supporting information
p. 453 - 459
(2013/04/23)
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- Arylation of chloroanthraquinones by surprisingly facile Suzuki-Miyaura cross-coupling reactions
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Chloroanthraquinones were found to undergo facile Suzuki-cross coupling with substituted phenyl boronic acids using a commercial catalyst Pd(PPh 3)4 and with Pd(PPh3)4 prepared in situ from Pd(PPh3)2Cl2 and PPh3.
- Thiemann, Thies,Tanaka, Yasuko,Iniesta, Jesus,Varghese, H. Tresa,Pannicker, C. Yohannan
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experimental part
p. 732 - 736
(2010/03/24)
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- Phenacenes from Diels-Alder trapping of photogenerated o-xylylenols: Phenanthrenes and benzo[e]pyrene bisimide
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The synthesis of phenanthrene and benzo[e]pyrene bisimides, 1 and 2, was accomplished via the Diels-Alder trapping of sterically congested o-xylylenols photochemically generated from 3,6-dibenzoyl-o-xylene and 1,4-dibenzoyl-9,10- dihydroanthracene, respec
- Ilhan, Faysal,Tyson, Daniel S.,Meador, Michael A.
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p. 577 - 580
(2007/10/03)
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- Reversal of the regioselectivity of anthrapyrazole formation. A new synthesis of Losoxantrone (DUP941)
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Losoxantrone, a potent anticancer agent, has been efficiently synthesized in a 6 step process from 5-hydroxy-1,4- dichloroanthracene-9,10-dione.
- Zhang, Lin-Hua,Meier, Walter E.,Watson, Elton J.,Gibson, Emily P.
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p. 3675 - 3678
(2007/10/02)
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- CONVENIENT SYNTHESIS ROUTES TO 1,4-DIFLUOROANTHRACENE-9,10-DIONE
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Two convenient synthetic routes to 1,4-difluoroanthracene-9,10-dione are described.
- Krapcho, A. Paul,Getahun, Zelleka
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p. 907 - 910
(2007/10/02)
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