Organic Cocrystals of TCNQ and TCNB Based on an Orthocetamol Backbone Solved by Three-Dimensional Electron Diffraction

Joseph E Hitchen, Iryna Andrusenko, Charlie Hall, Enrico Mugnaioli, Jason L Potticary, Mauro Gemmi, Simon R Hall*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

5 Citations (Scopus)
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We report the  rst co-crystals of TCNQ and TCNB based on orthocetamol, a regioisomer of paracetamol. Through a simple solution growth process, co-crystals were produced containing orthocetamol as electron donors, with co-formers of either 7,7,8,8-tetracyanoquinodimethane (TCNQ) or 1,2,4,5-tetracyanobenzene (TCNB), as electron acceptors. Due to sub-micron crystalline domains, 3D electron di raction was employed for structure solution in both systems. This revealed that both systems crystallise in a 1:1 stoichiometry, in which orthocetamol forms a backbone allowing for linking of acceptor molecules in a mixed-stack con guration. Orthocetamol-TCNQ adopts an non-centrosymmetric Pc symmetry, and orthocetamol-TCNB a centrosymmetric P-1 symmetry. UV-Vis and FT-IR were employed to probe the ability of these co-crystals to create CT systems, revealing a low degree of charge transfer. Still, the possibility to use orthocetamol backbone as structural sca old paves the way for an entirely new class of CT materials.
Original languageEnglish
Pages (from-to)1155–1163
Number of pages9
JournalCrystal Growth and Design
Issue number2
Early online date12 Jan 2022
Publication statusE-pub ahead of print - 12 Jan 2022

Bibliographical note

Funding Information:
S.R.H., J.P., J.H., and C.L.H. acknowledge the Engineering and Physical Sciences Research Council U.K. (Grants EP/G036780/1and EP/L015544/1), MagnaPharm, a collaborative research project funded by the European Union’s Horizon 2020 Research and Innovation programme (Grant 736899), and the Bristol Centre for Functional Nanomaterials and the Centre for Doctoral Training in Condensed Matter Physics. I.A., E.M., and M.G. acknowledge the Regione Toscana for funding the purchase of the Timepix through the FELIX project (Por CREO FESR 2014-2020 action).

Publisher Copyright:
© 2022 American Chemical Society.


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