Synthesis and characterization of dumbbell-like BTD-based derivatives to engineer organic building blocks in solid-state

• Published in: Journal of molecular structure 2018-02, Vol.1153, p.34-41
• Main Authors: Jiménez-Urias, Ana, Lugo-Aranda, Alejandra Zaavik, Miranda-Olvera, Montserrat, Farfán, Norberto, Santillan, Rosa, Arcos-Ramos, Rafael, Carreón-Castro, María del Pilar
• Format: Article
• Language: English
• Subjects: BTD derivatives; Molecular crystals; Organic semiconductors; Solid-state self-assembly; SXRD
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.09.106

Four BTD-derivatives 4, 5, 7 and 8 were synthesized and characterized by using solution NMR, FTIR and HRMS. In this study, BTD-central cores were supported on trityl type fragments in order to evaluate the influence of these groups prone to aggregation through interdigitation in the consolidation of ordered solids. Structural variation, between compounds 4–5 and 7–8, was selected by introducing aromatic phenyl rings at positions C-4 and C-7 of the BTD central core in order to increase the stackable surface. Crystals of compounds 4 and 5 were obtained and solved in the C2/c and P21/c space groups, respectively. Both crystalline arrays are dominated by CH⋯π and π-stacking interactions, desirable features for the bottom-up construction of highly polarizable organic crystals. The featured compounds with a dumbbell-like structure could be useful as scaffolds for self-assembled crystalline materials such as solid organic semiconductors. [Display omitted] •Four novel BTD-based organic building blocks were synthesized and characterized.•BTD-derivatives are synthetically accessible and solution processable.•Crystal structures 4 and 5 were solved in the C2/c and P21/c space groups.•Self-assembly is directed by non-classical H-bonding and π-stacking.•Interdigitation between BTD-based dumbbell-like molecules was found.