A new class of three-dimensional, p-type, spirobifluorene-modified perylene diimide derivatives for small molecular-based bulk heterojunction organic photovoltaic devices

Interest in bay‐substituted perylene‐3,4:9,10‐tetracarboxylic diimides (PDIs) for solution‐based applications is growing due to their improved solubility and altered optical and electronic properties compared to unsubstituted PDIs. Synthetic routes to 1,12‐bay‐substituted PDIs have been very demanding due to issues with steric hindrance and poor regioselectivity. Here we report a simple one‐step regioselective and high yielding synthesis of a 1,12‐dihydroxylated PDI derivative that can subsequently be alkylated in a straightforward fashion to produce nonplanar 1,12‐dialkoxy PDIs. These PDIs show a large Stokes shift, which is specifically useful for bioimaging applications. A particular cationic PDI gemini‐type surfactant has been developed that forms nonfluorescent self‐assembled particles in water (“off state”), which exerts a high fluorescence upon incorporation into lipophilic bilayers (“on state”). Therefore, this probe is appealing as a highly sensitive fluorescent labelling marker with a low background signal for imaging artificial and cellular membranes.

Section: Introductionmentioning

confidence: 99%

Synthesis and Self‐Assembly of Bay‐Substituted Perylene Diimide Gemini‐Type Surfactants as Off‐On Fluorescent Probes for Lipid Bilayers

Schill

Dun

Pouderoijen

et al. 2018

“…However, there are very limited examples of a single class of N^C‐chelate boron compounds that show tunable emission colors covering the entire visible spectrum. With our interests and previous works on various functionalized boron(III) compounds and spiro derivatives,, it was anticipated that the combination of the rigid nature of the N^C boron chelate and a bulky spiro structure can yield stable boron compounds with interesting photophysical properties. Herein, we report the design, synthesis, electrochemical, photophysical and electroluminescence properties of a new class of spiro‐containing N^C‐chelated four‐coordinate boron(III) compounds which exhibit very strong luminescence in both solution and solid‐state thin films.…”

Section: Introductionmentioning

confidence: 99%

Air‐Stable Spirofluorene‐Containing Ladder‐Type Bis(alkynyl)borane Compounds with Readily Tunable Full Color Emission Properties

Wong

et al. 2016

Self Cite

A series of air-stable spiro-fused ladder-type boron(III) compounds has been designed, synthesized, and the electrochemistry and photophysical behavior have been characterized. By simply varying the substituents on the pyridine ring and extending the π-conjugation of the spiro framework, the emission color of these compounds can be easily fine-tuned spanning the visible spectrum from blue to red. All compounds exhibit a broad and structureless emission band across the entire visible region, assigned as an intramolecular charge-transfer transition originating from the thiophene of the spiro framework to the pyridine-borane moieties. In addition, these compounds demonstrate high photoluminescence quantum yields of up to 0.81 in dichloromethane solution and 0.86 in doped thin films. Some of the compounds have also been employed as emissive materials, in which solution-processed organic light-emitting devices (OLEDs) with tunable emission colors spanning the visible spectrum from blue, green to red have been realized, demonstrating the potential applications of these boron compounds in OLEDs.

“…This stability makes PDIs excellent n‐type charge carriers [14] . Furthermore, PDI cores can also be self‐doped through bay and ortho substitution with electron‐donating or electron‐withdrawing moieties, [15] allowing their semiconductive behaviour to be tuned, even to exhibiting p‐type semiconductive behaviour [16] . Generally, the rigid PDI core minimises distortion during polaron migration, enabling efficient electron transfer and charge carrier mobilities comparable to those of amorphous silicon [17] .…”

Section: Introductionmentioning

confidence: 99%

Design and Control of Perylene Supramolecular Polymers through Imide Substitutions

Wilson-Kovacs

Fang

Hagemann

et al. 2021

The number and type of new supramolecular polymer (SMP) systems have increased rapidly in recent years. Some of the key challenges faced for these novel systems include gaining full control over the mode of self-assembly, the creation of novel architectures and exploring functionality. Here we provide a critical overview of approaches related to perylene-based SMPs and discuss progress to exert control over these potentially important SMPs through chemical modification of the imide substituents. Imide substitutions affect self-assembly behaviour orthogonally to the intrinsic optoelectronic properties of the perylene core, making for a valuable approach to tune SMP properties. Several recent approaches are therefore highlighted, with a focus on controlling 1) morphology, 2) H-or J-aggregation, and 3) mechanism of growth and degree of aggregation using thermodynamic and kinetic control. Areas of potential future exploration and application of these functional SMPs are also explored.