Influence of the heteroatom introduction on the physicochemical properties of 5-heterotruxenes containing nitrogen, oxygen and sulfur atom

Abstract

5-heterotruxenes are a class of heterocyclic aromatic compounds derived from the parent heptacyclic hydrocarbon, namely truxene. Currently, few substances belonging to this group are known. These include derivatives of 5-oxatruxene, 5-azatruxene, and 5-thiatruxene, along with its sulfone and sulfoxide. The introduction of one heteroatom, not only enables selective monofunctionalization of the 5-heterotruxene system but also allows adjustment of physico-chemical properties depending on the needs. Two investigated compounds, namely 5-oxatruxene and 5-azatruxene, exhibit fluorescence enhancement by symmetry breaking (FESB) phenomena, manifested by a fourfold increase in the fluorescence quantum yield. Therefore, derivatives of 5-heterotruxenes may contribute to the development of new stable optoelectronic substances as well as other functional materials. Nevertheless, in the beginning, it is crucial to investigate their spectral, thermal, and electrochemical properties to learn more about the advantages and limitations of these aromatic systems. The following article also presents a new simplified and universal synthetic methodology, without use of anhydrous conditions or organometallic substances, giving easy access to 5-azatruxene and structural-related heteroaromatic systems. The discussed heteroatom influence is not limited to the truxene core but also helps to understand the physicochemical properties of other, currently top-rated high-symmetric heteroaromatic systems such as circulenes, sumanenes and their analogues.