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

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 materials

Publication History

Received: 01 June 2021

Accepted: 13 July 2021

Accepted Manuscript online:
15 July 2021

Article published online:
12 October 2021

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