Abstract

Perylene-3, 4, 9, 10-bisimides (PBIs) are a family of classic functional dyes that are active in the fabrication of optic-electronic devices, such as non-fullerene acceptors in organic photovoltaics and n-type organic field effect transistors. Functionalization of PBIs with amidation or annulation not only modulates their intrinsic photochemical and photophysical performances but also brings new products of rylene family (e.g. terrylene diimides, coronenes). In this work, we introduce a new photo-synthetic method to produce annulated perylene bisimides with a 2-methylthiophene pendant at its bay position. Unlike the common photo-annulation that undergoes a 1, 6-2H elimination and forms a fused coronene structure, the proposed photo-synthesis presents a bisthienylethene-like cyclization with the H and methyl group toggling on each reaction carbon site. The 2-methylthiophene modified PBIs (PBI-MTs) exhibit fast photo-annulation (k = 4.3 × 10−1·s−1) with high conversion ratio (84%) under pure visible light irradiation (λ = 530 nm), which proves to be an effective and eco-friendly synthetic method for annulated PBI derivatives compared to the traditional UV-induced photosynthesis.

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