Florian Glöcklhofer

A Versatile One-Pot Access to Cyanoarenes from ortho- and para-Quinones: Paving the Way for Cyanated Functional Materials.

A generally applicable direct synthesis of cyanoarenes from quinones is presented. Particular emphasis is placed on the preparation of precursors and target molecules relevant for organic materials, including halogenated cyanoarenes and larger cyanated acenes. The reaction and work-up protocols are adjusted for the challenges presented by the different substrates and products. Screening results of the initial reaction optimization are given to further facilitate adaptation to other synthetic problems. The universality of the reaction is finally highlighted by successful substitution of para-quinones by an ortho-quinone as the starting material.

Multigram synthesis of bis[(trimethylsilyl)ethynyl]benzenes suitable for post-polymerization modification

Novel substituted bis[(trimethylsilyl)ethynyl]benzenes have been prepared as versatile building blocks for organic functional materials. The resulting effects of replacing sulfur by selenium and tellurium on photophysical and electrochemical properties have been examined. Polymerization via microwave-assisted Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and subsequent post-polymerization modification by oxidation reveals the utility of the developed building blocks.

Extending the Scope of a New Cyanation: Design and Synthesis of an Anthracene Derivative with an Exceptionally Low LUMO Level and Improved Solubility

The preparation of cyanated acenes from quinones has been improved for the conversion of electron-poor starting materials. The new procedure was used to prepare rationally designed 2,7-dinitro-9,10-dicyanoanthracene. Crystallographic, morphological, and electrochemical investigations have revealed most promising properties for applications in organic electronics.

Crystal structure of trans-1,4-bis­[(tri­methyl­sil­yl)­oxy]cyclo­hexa-2,5-diene-1,4-dicarbo­nitrile

The molecular structure of the title compound is centrosymmetric. The cyclohexa-2,5-diene moiety is exactly planar and has a bond-length distribution characteristic for one pair of double bonds and two pairs of single bonds.

Crystal structures of 2,5-di­azido-1,4-phenyl­ene di­acetate and 2,5-di­azido-1,4-phenyl­ene dibutyrate

2,5-Diazido-1,4-phenylene diacetate and dibutyrate are the first structurally characterized representatives with a trans-diazidophenylene entity. Both molecules possess inversion symmetry; however, the compounds crystallize in different crystal systems (triclinic versus monoclinic).

Synthesis of 1,2,5,6- and 1,4,5,8-anthracenetetrone: Building blocks for π-conjugated small molecules and polymers

Abstract Reliable reactions for the synthesis of two interesting anthracenetetrones have been identified and optimized. Both syntheses start from dihydroxy-9,10-anthraquinones and were selected for maximized efficiency and minimized workload. Work-up of all reactions can be achieved without column chromatography, which facilitates further scale-up. So far, both target compounds are considerably underexplored despite their promising molecular structure for use in devices and in organic synthesis, especially as building blocks for π-conjugated compounds. The crystal structure of 1,4,5,8-anthracentetrone is reported. Graphical Abstract

Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds

Abstract Highly fused, fully conjugated aromatic compounds are interesting candidates for organic electronics. With higher crystallinity their electronic properties improve. It is shown here that the crystallization of three archetypes of such molecules—pentacenetetrone, indigo, and perinone—can be achieved hydrothermally. Given their molecular structure, this is a truly startling finding. In addition, it is demonstrated that perinone can also be synthesized in solely high‐temperature water from the starting compounds naphthalene bisanhydride and o‐phenylene diamine without the need for co‐solvents or catalysts. The transformation can be drastically accelerated by the application of microwave irradiation. This is the first report on the hydrothermal generation of two fused heterocycles.

Novel 1,2,3-triazole based compounds as quadratic nonlinear optical crystals

Systematic investigations towards a novel class of quadratic NLO materials, based on the application of 1,2,3-triazole moieties, are outlined to afford organic crystals displaying SHG nonlinearities of more than 9 times the value of KDP.