- Facile synthesis and theoretical conformation analysis of a triazine-based double-decker rotor molecule with three anthracene blades
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The facile synthesis of a rotor-shaped compound with two stacked triazine units, which are symmetrically connected by three anthracene blades through oxygen linkers, is presented. This new double-decker, which is a potential monomer for two-dimensional polymerization, was synthesized by using readily available, cheap building blocks, exploiting the known selectivity difference for the nucleophilic substitution of cyanuric chloride. The crystal structure of a C3h symmetric rotor-shaped compound with 9,10-dihydroanthracene blades, which is a direct precursor to the targeted monomer, and the crystal structure of the new double-decker with the desired C3h symmetry, are also reported. The synthetic efforts were preceded by a computational analysis, which was triggered by the question of conformational stability of the potential monomer. Two stable conformers could be found, and the barrier for the transition path in the gas phase between these conformers was determined by quantum chemical calculations. Exploratory Born-Oppenheimer molecular-dynamics simulations revealed a strong influence of solvent-solute interactions on the stability of the conformers, which resulted in an energetic preference of the C3h symmetric conformation of the double-decker.
- Kory, Max J.,Bergeler, Maike,Reiher, Markus,Schlueter, A. Dieter
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- Synthesis of a Monomer for Two-Dimensional Polymerization under Technically Feasible Conditions
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The synthesis of a promising 2D polymer uses the double decker rotor-shaped monomer 1, containing three anthracene moieties. To accelerate the development of the field of 2D polymers, this monomer was selected for scale-up that would allow its synthesis to be performed on the kg scale under technical conditions. This goal was achieved in collaboration with Polymaterials AG, Kaufbeuren, Germany. Not only was the synthetic route shortened, but each and every aspect of the remaining steps was streamlined so as to render them applicable to technical conditions. This involved the entire sequence to be adapted to metal instead of glass reactors and to a number of safety and toxicity concerns. Additionally, not only the utilization of the reactors had to meet strict efficiency requirements, but also the work-up procedures had to be facile. The whole sequence was then tested for feasibility under realistic conditions at Polymaterials AG. While this test afforded 130?g of monomer 1, it has the clear potential for the kg scale, supposed the safety equipment for the hydrogen evolution for the conversion of compound 2a?–?3 is available.
- Tanner, Philipp,Maier, Gerhard,Schlüter, A. Dieter
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- Fluorescent molecule for identifying mercury ions as well as preparation method and application
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The invention discloses a fluorescent molecule for identifying mercury ions as well as a preparation method and application. Polycyclic aromatic hydrocarbons including a naphthalene ring or an anthracene ring and the like are used as starting raw materials and different identification sites are connected through a series of organic synthetic reaction (including substitution and addition) to obtainmolecular-tweezers-shaped main body compounds with different identification properties. The fluorescent molecule can be used for detecting the mercury ions and the problem that guest molecules cannotbe easily effectively identified through an existing molecule device is solved.
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Paragraph 0073; 0074; 0075; 0076
(2019/01/08)
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- Synthesis of novel H-shaped chromophores
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A series of H-shaped chromophores with two parallel and non-conjugated D-π-A units have been synthesized, in which a 9,10-dihydroanthracene was employed as molecular backbone. The synthesis of these H-shaped chromophores 9a-11a was accomplished via an eight-step reaction, including double Claisen rearrangement, hydroboration-oxidation, Rieche formylation reaction, Knoevenagel condensation and Corey-Fuchs reaction, with a total yield about 12.5%. The corresponding mono-D-π-A unit compounds 9b-11b were also prepared in a similar procedure for the purpose of comparison. Crystal structures of three intermediates 5a, 7a and 8a were measured, which demonstrate that the two D-π-A units in a single H-shaped chromophore molecule are nearly arranged at the same direction. The studies of UV-vis spectra and the solvatochromic method indicate that the molecular second-order polarizabilities values (μβ) of H-shaped chromophores are remarkably increased compared with the corresponding mono-D-π-A unit reference compounds, without causing a large shift of the absorption band to longer wavelength.
- Shi, Jie-Ping,Wu, De-Lin,Ding, Yong,Wu, Dong-Hua,Hu, Hong-Wen,Lu, Guo-Yuan
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scheme or table
p. 2770 - 2777
(2012/04/23)
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- An easy and multigram scale synthesis of anthracene-1,8-ditriflate
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1,8-Ditriflated anthracene was prepared by an easy and straightforward approach that enables its reproducible synthesis on a 10 gram scale. Its symmetric/unsymmetric diethynylations by using the Sonogashira cross-coupling reactions were also demonstrated. Georg Thieme Verlag Stuttgart.
- Kissel, Patrick,Weibel, Fabian,Federer, Lukas,Sakamoto, Junji,Schlüter, A. Dieter
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experimental part
p. 1793 - 1796
(2009/05/09)
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