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Structure and Phase Transition of 4,7-Bis-(4′-cyano-biphenyl-4-yl)-[1, 10]phenanthroline

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Abstract

4,7-Bis-(4′-cyano-biphenyl-4-yl)-[1, 10]phenanthroline (cnbiphphen) is synthesized from a palladium mediated coupling between 4-cyanobenzene boronic acid and 4,7-bis(4-bromophenyl)-[1,10]phenanthroline. The single crystal X-ray structure was measured at both 298(2) K and 90(2) K. The asymmetric unit of the title compound in the low-temperature phase, C38H22N .4 HCCl3, is comprised of one cnbiphphen molecule and one chloroform solvent molecule. Additional symmetry relates one-half of the title compound to the other at room temperature. During cooling the structure experiences a reversible phase transition from A 2/a (different setting of C 2/c, with a and c exchanged to match lattice parameters of both phases) to P 21/c. The crystal packing of the title compound consists primarily of electronic charge interactions between the cyano moieties. The chloroform solvent mol-ecule is situated in a cavity between two phenanthroline systems and is associated to two nitrogen atoms of cnbiphphen molecules through Cl3C–H⋯Nphen van der Waals interaction.

Graphical Abstract

The synthesis, structure, analytical characterization, optical properties and phase transition of 4,7-bis-(4’-cyano-biphenyl-4-yl)-[1,10]phenanthroline is presented.

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Acknowledgments

The authors wish to thank Andranik Aprikyan and Kilian Dill of Stemgenics for the use of their spectrophotometer.

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Authors and Affiliations

  1. Seattle Polymer Company, 454 North 34th Street, STE 100, Seattle, WA, 98103, USA

    Brenden Carlson

  2. X-ray Laboratory, Chemistry Department, University of Washington, Box 351700, Seattle, WA, 98195, USA

    Werner Kaminsky

  3. Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY, 13902, USA

    Linyue Tong

  4. Chemistry Department, State University of New York College at Cortland, Cortland, NY, 13045, USA

    Gregory D. Phelan

Authors
  1. Brenden Carlson
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  2. Werner Kaminsky
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  3. Linyue Tong
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  4. Gregory D. Phelan
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Corresponding author

Correspondence to Brenden Carlson.

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Carlson, B., Kaminsky, W., Tong, L. et al. Structure and Phase Transition of 4,7-Bis-(4′-cyano-biphenyl-4-yl)-[1, 10]phenanthroline. J Chem Crystallogr 45, 453–460 (2015). https://doi.org/10.1007/s10870-015-0614-y

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  • DOI: https://doi.org/10.1007/s10870-015-0614-y

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