Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future

Abstract

Perylene dyes have transcended their role as simple colorants and have been reinvigorated as functional dyes. Based on the substitution at the peri position by six-membered carboxylic imides, the perylene family is principally embellished with perylene diimides (PDIs) and perylene monoimides (PMIs). Perylene dyes are widely acclaimed and adorned on account of their phenomenal thermal, chemical, and photostability juxtaposed with their high absorption coefficient and near-unity fluorescence quantum yield. Although symmetric PDIs have always been in the limelight, its asymmetrical counterpart PMI is already rubbing shoulders, thanks to the consistent efforts of several scientific minds. Recently, there has been an upsurge in engendering PMI-based versatile organic architectures decked with intriguing photophysical properties and pertinent applications. In this review, the synthesis and photophysical features of various PMI-based derivatives along with their relevant applications in the arena of organic photovoltaics, photocatalysis, self-assembly, fluorescence sensing, and bioimaging are accrued and expounded, hoping to enlighten the less delved but engrossing realm of PMIs.

Phenylene‐Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure–Property Relationship

“…[10] At the same time, perylene monoimide (in this work abbreviated as "P") has attracted less research attention. [11] Perylene monoimides also have a strong absorption in the visible range, but have higher lying LUMO energy levels (lower reduction potentials) than perylene diimides. [12] This enables reaching of higher open circuit voltages (V OC ) in solar cells.…”

Tumor microenvironment-activated multi-functional nanodrug with size-enlargement for enhanced cancer phototheranostics

“…With the sterically hindered drug Chl attached, the π-π stacking effect of CPMI was weakened. 41,42 As a result, NPMI easily aggregated into larger particles. Therefore, the release of NPMI upon the TME response would induce the size-enlargement of the nanodrug.…”

Sulfone-Modified Perylene Acceptors with Improved Permittivity for Bilayer Organic Solar Cells Processed from Non-halogenated Solvents

“…In recent works, , we already prepared A-D-A type acceptors comprising perylene monoimide (PMI) as end groups and electron rich donors (fluorene, carbazole, indenofluorene). PMI derivatives have not only a strong UV–Vis absorption and high thermal and photochemical stability but can also be modified easily due to their straightforward synthetic preparation. , By switching the side chain on the linker to diethylene glycol, we already showed that the permittivity can be improved . Here, we shifted our focus to sulfone-based side chains.…”