Peri-alkylated terrylenes and ternaphthalenes building-blocks towards multi-edge nanographenes

Chemistry. 2024 Apr 25:e202401462. doi: 10.1002/chem.202401462. Online ahead of print.

Abstract

Since its first synthesis by Clar in 1948, terrylene - a fully connected ternaphthalene oligomer via naphthalene's peri-positions - has gained special focus within the rylene family, drawing interest for its unique chemical, structural, optoelectronic and single photon emission properties. In this study, we introduce a novel synthetic pathway that enhances the solubility of terrylene derivatives through complete peri-alkylation, while also facilitating extensions at the bay-positions. This approach not only broadens the scope of terrylene's chemical versatility but also opens new avenues for developing solution processable novel multi-edge nanographenes and tailoring electronic energy levels through topological edge structures. Our findings include a comprehensive structural and spectroscopic characterization which include transient absorption spectroscopy and photophysics of both the synthesized peri-alkylated terrylene and its phenylene-fused derivative.

Keywords: Bay-extension of Terrylene; Multi-edge Nanographenes; Peri-alkylation of Rylene; Terrylene; Transient Absorption Spectroscopy.