The influence of strong and weak hydrogen bonds on the solid state arrangement of hydroxy-containing boron subphthalocyaninesElectronic supplementary information (ESI) available: Experimental details and additional molecular packing arrangement figures, as well as displacement ellipsoid plots, bond lengths, crystal data and structure refinement for compounds 2 and 3a-3c. CCDC reference numbers 949038-949043. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3c

• Main Authors: Virdo, Jessica D, Crandall, Laura, Dang, Jeremy D, Fulford, Mabel V, Lough, Alan J, Durfee, William S, Bender, Timothy P
• Format: Article
• Language: English
• ISSN: 1466-8033
• DOI: 10.1039/c3ce41412d

We have investigated the occurrence of hydrogen bonding in boron subphthalocyanine (BsubPc) derivatives by synthesizing a series of four hydroxy-containing BsubPcs and studying their solid state arrangements using X-ray diffraction. The series of derivatives comprises hydroxy-BsubPc (HO-BsubPc) as well as para -, meta -, and ortho -hydroxy-phenoxy-BsubPc ( p -, m - and o -HOPhO-BsubPc). Each solid state arrangement demonstrated both strong (O-H N, O-H O) and weak (C-H O, C-H N) hydrogen bonds, with the structure for o -HOPhO-BsubPc including examples of bifurcated hydrogen bonds. Many of the C-H O interactions were found to occur alongside notable perturbations to the expected intra- and intermolecular geometry of BsubPcs, providing structural evidence for the significance of weak C-H O bonds. We observed that the imine nitrogen atom of the BsubPc moiety is a reliable hydrogen bond acceptor, and in most arrangements, the hydroxy moiety participated in hydrogen bonds both as a donor and an acceptor. The presence of hydrogen bonds in addition to other intermolecular interactions (π-π and CH-π, which are common in BsubPc solid state arrangements) facilitates the arrangement of BsubPc into two- and three-dimensional networks of closely associated molecules. Strong (O-H N, O-H O) and weak (C-H O, C-H N) hydrogen bonds direct the arrangement of hydroxy-containing boron subphthalocyanine (BsubPc) derivatives into two- and three-dimensional network motifs.