Abstract
Rubrene (5,6,11,12-tetraphenyltetracene) is a polyacene material that has been well
studied throughout its nearly one-hundred year history. Originally found fascinating
for its luminescent properties, it has emerged at the forefront for organic electronics
due to its particularly high charge carrier mobility for an organic crystal. Despite
great interest and its explosion in the literature over the past two decades, the
commercial synthesis of rubrene has remained relatively unchanged since its initial
discovery in 1926. Several recent studies have reported alternate routes to the rubrene
structure with substitutions on the peripheral aromatic rings and tetracene core.
Substituting in this manner has the potential to improve upon rubrene’s electronic
properties. We review the various routes to rubrene and its derivatives and provide
a brief overview of the solid-state library available for study. The information gained
by comparing the solid-state properties between derivatives offers insight into unpredictable
crystallization and polymorphism – complicated issues – which have hindered research
into materials applications of rubrene. We hope that these insights inspire work
in application-driven synthetic chemistry for future rubrene derivatives.
1 Introduction
2 Synthesis
2.1 Traditional Rubrene Synthesis
2.1.1 Recent Applications
2.2 Multi-Step Synthesis
2.2.1 Historical Routes
2.2.2 Diels–Alder Approaches
2.2.3 Cross-Coupling Approaches
2.2.4 Comparative Synthesis of Perfluororubrene
3 Crystal Engineering
4 Conclusions and Outlook
Key words
rubrene - crystal engineering - comparative synthesis
