SYNTHESIS OF SOLUBLE AND STABLE HIGH ORDER ACENES

Abstract

The current work discusses the synthesis of stable and soluble high order acenes based on a new architecture designed, considering three major aspects that affect the performance of acene based materials in their applications, viz., solubility, stability and molecular order. Using the developed protocol a series of cyclopentadiene-fused acenes from anthracene to undecacene has been synthesized and characterized to understand the physicochemical properties of the synthesized acenes. The current strategy proved to considerably improve the stability of acene derivatives compared to the reported analogs. For the first time, the synthesis of acene longer than nonacene, i.e., undecacene, has been reported in this study. Interestingly CP-fused high order acenes such as heptacene, nonacene and undecacene show significant diradical character, yet remain appreciably stable in the ambient conditions. The current strategy can be successfully extrapolated to synthesize highly stable and soluble high order oligoacenes and possibly polyacene to realize their novel applications.