Triarylborane-terminalized branched π-conjugative dyes: Synthesis, structure and optoelectronic properties

• Three triarylborane-ended branched compounds have been designed and synthesized.
• These compounds displayed intense fluorescence both in THF and in solid state.
• Their high redox reversibility made them promising light-emitting materials.

Organic optoelectronic materials with high fluorescence quantum yield, both in solution and in the solid state, have attracted considerable interest in recent years. In this work, we designed and synthesized three triarylborane-terminalized branched π-conjugative compounds, including two C3-symmetric π-3A(acceptor) triarylboron dyes: 2,7,12-tri(5-(dimesitylboryl)thiophen-2-yl)-5,5′,10,10′,15,15′-hexaethyltruxene and 2,7,12-tri((5-(dimesitylboryl)thiophen-2-yl)ethynyl)-5,5′,10,10′,15,15′-hexaethyltruxene, and a 2D(donor)-π-A asymmetric dye: 2,7-di(N,N-diphenylamino)-12-(5-(dimesitylboryl)thiophen-2-yl)-5,5′,10,10′,15,15′-hexaethyltruxene. The three compounds displayed prominent optical properties. The ethynyl spaced thiophene analogue emitted intense fluorescence both in the THF solution and in the solid state with excellent quantum yields. Interestingly, their solid powders showed a very different fluorescence colour from their respective THF solution. The results of theoretical calculations were in good agreement with the experimental absorption and CV spectra. The high reversibility of the three boron-containing dyes in their redox process indicates substantial stability of the produced species, which make them promising light-emitting materials.

Figure optionsDownload as PowerPoint slide