Template-Induced Crystallization of Novel Orthorhombic 9,10-Diphenylanthracene Polymorph

Abstract

Polymorphism in organic semiconductor materials has attracted great interest due to the potential for tuning both structure and optoelectronic properties for next-generation optoelectronic devices. Therefore, developing methods to control the solution crystallization process is important for improving the kinetics of crystal nucleation and obtaining the desired functional systems. Template-induced crystallization is an intriguing crystallization control approach that enables heterogeneous nucleation of the solute on template surfaces, either intentionally introduced into the system or naturally occurring during crystallization. Here, we studied template-induced crystallization of the organic luminophore 9,10-diphenylanthracene (DPA) on the following crystals used as substrates: pyrene, perylene, anthracene, and rubrene. Crystallization of DPA in the presence of pyrene and perylene resulted in the formation of their cocrystals, whereas crystallization with anthracene and triclinic rubrene crystals had no effect on DPA polymorphism. We found that, in the presence of orthorhombic rubrene used as a template, a novel orthorhombic DPA polymorph (δ-DPA) crystallized. δ-DPA has herringbone packing similar to that of the used template. δ-DPA crystals demonstrated blue emission with a photoluminescence quantum yield of 52% and needlelike morphology. The results obtained could be used for crystallization control and engineering of high-performance conjugated crystalline materials.