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DOI: 10.1055/a-1551-6930
Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future
![](https://www.thieme-connect.de/media/10.1055-s-00040992/202103/lookinside/thumbnails/10-1055-a-1551-6930_om0035-1.jpg)
Dedicated to Prof. Heinz Langhals and Prof. Jonathan S. Lindsey.
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
Key words
rylene dyes - perylene monoimide - self-assembly - fluorescent probe - functional organic materialsPublication History
Received: 01 June 2021
Accepted: 13 July 2021
Accepted Manuscript online:
15 July 2021
Article published online:
12 October 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (>https://creativecommons.org/licenses/by-nc-nd/4.0/)
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