Synthesis and characterization of 2,6-bis(arylethynyl)anthraquinones.

摘要

Over the past decade, a large number of investigations have been conducted in the field of organic semiconductors (OSCs). These semiconductors can be classified into three different categories: small organic molecules, short chain (oligomers) and long chain (organic polymers). Ideally, organic materials that are used in semiconductors should have an inexpensive price, be lightweight and flexible. The three most common applications of OSCs are organic photovoltaics (OPVs), organic light-emitting diodes (OLEDs), and organic field transistors (OFETs).;The keys that are playing an important role on electronic device functionality are: HOMO-LUMO band gap, which should be in the range of 1.5-3 eV; Organic crystal packing, which influences the charge mobility.;Small organic molecules like acenes (naphthalene, anthracene, etc.) act well and have advantages like the simple manner to make or modify the compounds. In addition, the chemical structure can be easily defined and high purities can be reached.;Anthraquinones, which are used for dye materials, are recognized to undergo reversible reductions. Several recent studies explored the use of 2,6-anthraquinones for electron capture applications. Building on this, our project is focused on the use of anthraquinones as potential electron acceptors for organic semiconductors (OSCs). In order to reach this target, we started to synthesize a series of 2,6-bis(arylethynyl)-anthraquinones. The synthesis of three analogs was attempted, with Sonogashira coupling as the significant step. In addition, preliminary characterization of he optical properties and electrical potentials for these compounds was conducted. Specifically, we wished to determine whether substitution in the 2,6-positions using simple aryl substituents could produce compounds which were competitive with the most well-known organic acceptor compounds such as C60 and fullerene derivatives.