Synthesis and photovoltaic application of NIR-emitting perylene-monoimide dyes with large Stokes-shift

Abstract

A series of NIR emitting perylene-monoimide (PMI) dyes were developed via tetra alkynylation of PMI(Br)4 at bay and peri positions using Sonogashira coupling protocol for organic photovoltaics application.

1,7,9,10‐Tetrasubstituted PMIs Accessible through Decarboxylative Bromination: Synthesis, Characterization, Photophysical Studies, and Hydrogen Evolution Catalysis

“…[36] Koner et al adopted the idea of using multiple brominated perylenem onoimides (PMI) to introduce different electron-donating groupst ot he perylene scaffold by synthesizing 1,6,9,10-tetrabromoP MI with 46 %y ield followed by nucleophilic aromatic substitutions with different substituted phenolsand thiophenols. [37,38] Although many of these earlier works have demonstrated the potentialo ft he rylene scaffold, some of the procedures use up to 200 equivalents of bromine during the synthesis which could effectively preventa ny possible large-scale applications.T herefore, in the search for novel photoactive materials, the discovery of straightforward synthetic procedures that give the desired photosensitizers in high yields and use more environmentally friendly procedures is essential to be ablet oc reate safe and ecofriendly alternatives to fossil fuels.…”

Computer vision vs. spectrofluorometer-assisted detection of common nitro-explosive components with bola-type PAH-based chemosensors

“…[23][24][25] Among many uorescent chemosensors, 26 PAH-based (multi)uorophore ones have attracted much attention due to their remarkable uorescent properties, such as ability to form excimers 27 either in a solution 28 or in a gas phase, 29 with a strong emission. PAHs are common components for NIR dyes, 30 OLEDs, 31 LC displays, 32 and batteries, 33 as well as photoresponsive materials 34 and photovoltaic devices. 30 Excimer emission of PAH-based uorophores is a convenient tool for the analysis of water or food samples, 35 for DNA studies, 36 as well as for the "turn-off' detection of various analytes/pollutants, 37 including (nitro)explosives.…”

“…PAHs are common components for NIR dyes, 30 OLEDs, 31 LC displays, 32 and batteries, 33 as well as photoresponsive materials 34 and photovoltaic devices. 30 Excimer emission of PAH-based uorophores is a convenient tool for the analysis of water or food samples, 35 for DNA studies, 36 as well as for the "turn-off' detection of various analytes/pollutants, 37 including (nitro)explosives. 38,39 In the last case the uorescence quenching of PAH uorophores via either charge or energy transfer is easily registered by a uorimeter.…”

Aggregation Induced Emission Switching Based Ultrasensitive Ratiometric Detection of Biogenic Diamines Using a Perylenediimide-Based Smart Fluoroprobe

“…are employed for the quantitative and qualitative detection of BAs. − However, these analytical methods require a long analysis time . Instead, optical detection methods using a stable emissive probe are highly promising due to their high selectivity and sensitivity. ,, Among the existing methods, ratiometric sensors enable the detection of emission intensity in solution simultaneously at two different wavelengths and have an additional advantage of being devoid of intensity and instrument dependence. ,, For practical applications, vapor sensing is more convenient and preferable and its detection still remains challenging due to the limited availability of fluorescent sensors for solid-state applications. − Among the various types of reported fluorescent sensors, perylene dyes exhibit a combination of desirable features, including a near-unity fluorescence quantum yield (QY) and excellent thermal, chemical, and photochemical stability. − The incorporation of substituents at the bay and peri positions of PDI bring about desirable chemical and photophysical properties via a self-assembly process and has been used for various applications. ,,− …”