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

Glöcklhofer, Florian; Morawietz, Andreas J.; Stöger, Berthold; Unterlass, Miriam M.; Fröhlich, Johannes

doi:10.1021/acsomega.7b00245

Cited by 21 publications

(17 citation statements)

References 25 publications

(54 reference statements)

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“…The required precursors 2a-b were obtained by methylation of the respective hydroxyanthraquinones 1a-b. Although the new cyanation was previously demonstrated to proceed well also with functional groups attached to the anthraquinone, 21 the electron-donating character of the methoxy groups of 2a-b initially impeded successful cyanation. Reduced temperatures and increased reaction times solved this issue.…”

Section: Synthesismentioning

confidence: 99%

Effect of symmetric and asymmetric substitution on the optoelectronic properties of 9,10-dicyanoanthracene

Glöcklhofer

Rosspeintner

Pasitsuparoad

et al. 2019

Mol. Syst. Des. Eng.

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Section: Synthesismentioning

confidence: 99%

Effect of symmetric and asymmetric substitution on the optoelectronic properties of 9,10-dicyanoanthracene

Glöcklhofer

Rosspeintner

Pasitsuparoad

et al. 2019

Mol. Syst. Des. Eng.

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“…our recently developed method for the synthesis of substituted 9,10-anthracenedicarbonitriles (also known as 9,10dicyanoanthracenes). [10][11][12][13][14] However, as with our method, most available synthetic methods yield anthracene derivatives with substituents in the central 9-and 10-positions. The preparation of anthracene derivatives without substituents in these positions is often more challenging.…”

Section: Introductionmentioning

confidence: 99%

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

et al. 2020

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Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach. File list (3) download file view on ChemRxiv Draft_final.pdf (351.19 KiB) download file view on ChemRxiv SI_final.pdf (550.08 KiB) download file view on ChemRxiv all.cif (559.68 KiB)

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“…Having experimental data about Miller indices of crystal faces, one can examine corresponding planes using the free Packing/Slicing tool of Mercury. Particularly, indexing of the crystal phases becomes of practical interest for nonlinear optics [120], organic photonics [121], piezoelectrics [122][123][124], and organic electronics [125][126][127][128]. Knowledge of functional groups or supramolecular synthons forming crystal faces allowed in some cases to rationalize mechanical effects in dynamic crystals [129][130][131][132] such as self-healing, jumping, bending, twisting at heat, humidity, force or light, and to describe pressure-induced phase transitions (see Refs.…”

Section: Bfdh Morphology Predictionmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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

Cited by 21 publications

References 25 publications

Effect of symmetric and asymmetric substitution on the optoelectronic properties of 9,10-dicyanoanthracene

Effect of symmetric and asymmetric substitution on the optoelectronic properties of 9,10-dicyanoanthracene

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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