From flat to twisted – multifunctional phosphacyclic nanocarbons based on Vat Orange 3

Abstract

The field of π-conjugated organic materials has seen significant advances in recent years. However, enhancing the functionality of well-established, mass-produced compounds remains a considerable challenge, despite being an intriguing strategy for designing high-value organic materials with low production costs. In this context, vat dyes, known for their wide range of colors and extensive use in the textile industry are particularly attractive. Here, we present an innovative approach that conjoins phosphorus heterocycles with the dye Vat Orange 3 (VO3) to yield novel nanocarbons with enhanced functional properties. X-ray crystallography reveals distinct twisting of the scaffold in the solid state, while the modification of the phosphorus centers leads to intriguing and versatile photophysics. Thin-film analyses show unusual, pronounced emission features that switch from green to orange upon aggregation. Furthermore, Lewis-adduct formation induces a fluorescence redshift upon coordination to the phosphorus moiety and cyclic voltammetry confirms the acceptor character of the system. This work demonstrates the versatility of phosphorus-modified vat dyes as value-added organic compounds and paves the way for the development of new functional 2D nanocarbons with broad technological relevance.