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

Abstract

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, their 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 bio-imaging are accrued and expounded, hoping to enlighten the less delved but engrossing realm of PMIs. Table of content: 1 Introduction 2 Advantages of PMI over PDI 3 Challenges in Working with PMI and Ways to Overcome 4 Various Aspects of Reactivity of Different Positions 5 Synthesis of the PMI core 6 Synthesis of PMI Derivatives 6.1 Bromination of PMI 6.2 Synthesis of PMI Derivatives using Coupling Reactions 6.2.1 Suzuki Coupling 6.2.2 Sonogashira Coupling 6.2.3 Buchwald–Hartwig Coupling Reaction 6.3 Nucleophilic Substitution Reactions 6.4 Peri-Annulation Reaction 7 Photophysical Properties of PMI 8 Singlet Fission Properties 9 Förster Resonance Energy Transfer with PMI 10 Symmetry Breaking Charge Transfer Properties 11 Panchromatic Light Absorption Properties of PMI 12 Acid/Base Sensitivity of PMI 13 NIR-Absorbing PMI 14 Achieving of Triplet State Using PMI 15 Solid-State Emissive PMI 16 Thermo-Responsive Materials with PMI 17 Photo-Responsive PMI Derivatives 18 Electrochemical Properties of Rylene Derivative 19 Self-Assembling Properties of PMI Derivatives 20 Applications of PMI in Solar Cells 21 PMIs in Bulk Heterojunction Solar Cells 22 PMIs in Dye-Sensitized Solar Cells 23 PMI as a Fluorescent Reporter 23.1 Application of PMI Derivatives for Bio-Imaging 23.2 Hydrophilic PMIs for Bio-Imaging 23.3 Aggregated PMI as NIR-Emissive Fluoroprobe for Bio-Imaging 24 Photocatalytic Hydrogen Generation using PMI 25 PMI-Based Organocatalysis 26 PMI Derivatives for Single-molecule Spectroscopy 27 Host–Guest Chemistry with PMI 28 Conclusions and Outlook

Keywords

• rylene dyes
• perylene monoimide
• self-assembly
• fluorescent probe
• functional organic materials