Large Non-planar Conjugated Molecule with Strong Intermolecular Interactions Achieved with Homoleptic Zn(II) Complex of Di(5-quinolylethynyl)-tetraphenylazadipyrromethene

Chenwei Lu; Chunlai Wang; Jayvic C Jimenez; Arnold L Rheingold; Genevieve Sauvé

doi:10.1021/acsomega.0c05169

Large Non-planar Conjugated Molecule with Strong Intermolecular Interactions Achieved with Homoleptic Zn(II) Complex of Di(5-quinolylethynyl)-tetraphenylazadipyrromethene

ACS Omega. 2020 Nov 25;5(48):31467-31472. doi: 10.1021/acsomega.0c05169. eCollection 2020 Dec 8.

Authors

Chenwei Lu¹, Chunlai Wang¹, Jayvic C Jimenez¹, Arnold L Rheingold², Genevieve Sauvé¹

Affiliations

¹ Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44122, United States.
² Department of Chemistry and Biochemistry, University of California San Diego, La Jolla California, 92093, United States.

Abstract

Zinc(II) complexes of tetraphenylazadipyrromethenes are potential non-planar n-type conjugated materials. To tune the properties, we installed 5-quinolylethynyl groups at the pyrrolic positions. Compared to the complex with 1-napthylethynyl, we found evidence for stronger intermolecular interactions in the new complex, including much higher overlap integrals in crystals. X-ray analysis revealed unconventional C-H···N hydrogen bonding between two quinolyls of neighboring molecules, pointing to a new strategy for the development of non-planar molecular semiconductors with stronger intermolecular interactions.