Aromatic interactions of allenyl-anthracene derivatives with pi-electron acceptor molecules: an experimental and computational study

ABSTRACT

Electrostatic effects play an important role in aromatic interactions towards molecular recognition. Anthraceno-allenophanes are cyclic π-conjugated aromatic systems able to recognise complementary molecules through aromatic interactions. A computational and experimental study has shown that the dispersive contribution is the predominant stabilising term in the interaction of an allenyl-anthracene derivative with relevant π-acceptor molecules, such as pentafluorophenol, picric acid and 2,3-dichloro-5,6-dicyano-1,4-quinone.

Graphical Abstract

KEYWORDS:

• Aromatic interactions
• anthracene derivatives
• molecular recognition
• SAPT
• π-acceptor molecules

Acknowledgments

This work was financially supported by Ministerio de Economia y Competitividad of Spain (CTQ2017-85919-R) and Xunta de Galicia (ED431C 2017/7 and CITACA Strategic Partnership: ED431E 2018/07).Centro de Supercomputación de Galicia (CESGA) is also acknowledged. M. M-L thanks Xunta de Galicia for a postdoctoral contract (ED481B 2016/166-0).

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplementary material

Supplemental data for this article can be accessed here.

Additional information

Funding

This work was supported by the Consellería de Cultura, Educación e Ordenación Universitaria, Xunta de Galicia [ED431E 2018/07,ED431C 2017/7,ED481B 2016/166-0]; Ministerio de Economía, Industria y Competitividad, Gobierno de España [CTQ2017-85919-R].