Protein‐like Enwrapped Perylene Bisimide Chromophore as a Bright Microcrystalline Emitter Material

Abstract

Strongly emissive solid‐state materials are mandatory components for many emerging optoelectronic technologies, but fluorescence is often quenched in the solid state owing to strong intermolecular interactions. The design of new organic pigments, which retain their optical properties despite their high tendency to crystallize, could overcome such limitations. Herein, we show a new material with monomer‐like absorption and emission profiles as well as fluorescence quantum yields over 90 % in its crystalline solid state. The material was synthesized by attaching two bulky tris(4‐tert‐butylphenyl)phenoxy substituents at the perylene bisimide bay positions. These substituents direct a packing arrangement with full enwrapping of the chromophore and unidirectional chromophore alignment within the crystal lattice to afford optical properties that resemble those of their natural pigment counterparts, in which chromophores are rigidly embedded in protein environments.

Suppressing Solid-State Quenching in Red-Emitting Conjugated Polymers

“…Intermolecular communication and ACQ can be suppressed by spatially isolating individual chromophores. Three important strategies employed to supress ACQ in conjugated materials are; (a) non-covalent threading through a macrocycle, 10,11 (b) incorporation of steric bulk 12,13 and (c) covalent encapsulation through alkylene straps [14][15][16][17] (Figure 1). In the past, most encapsulated conjugated materials have been prepared via non-covalent approaches, so as to form rotaxanelike materials.…”

“…A recent paper by Würthner and coworkers highlights the potential of this strategy. 13 ACQ was almost completely supressed in a perylene diimide (PDI) dye, which exhibited a solid state FF of over 90%. 13 However, this approach does not always sufficiently limit electronic cross communication, 19 and to the best of our knowledge only very few have been successful in obtaining high values of FR for red emitters through employing steric bulk effects.…”

“…13 ACQ was almost completely supressed in a perylene diimide (PDI) dye, which exhibited a solid state FF of over 90%. 13 However, this approach does not always sufficiently limit electronic cross communication, 19 and to the best of our knowledge only very few have been successful in obtaining high values of FR for red emitters through employing steric bulk effects. [20][21][22] The third method relies on covalent encapsulation, which has become increasingly popular in the last few years.…”

Ultrabright Fluorescent Polymeric Nanofibers and Coatings Based on Ionic Dye Insulation with Bulky Counterions

“…Several approaches such as introduction of spiro-framework 28,29 , bulky group substitution [30][31][32] , J-aggregate formation 33 , introduction of non-planar groups 34,35 , supramolecular threading, 36 etc., have been put forward to attenuate the ACQ phenomena and to improve the brightness of the luminescent materials both in the case of molecular dyes as well as in polymeric nanomaterials.…”

Red Organic Light-Emitting-Diodes based on a N-Annulated Perylene Diimide Dimer

“…The perylene diimide (PDI) chromophore is one of the best candidates to construct new emitters for solution-processed red OLEDs owing to a pure red colour, high quantum yield photoluminescence, and high thermal and photochemical stability [15][16][17] . Furthermore, PDIs can be rendered soluble in a range of solvents and thus are suitable for large area roll-to-roll coating [18][19][20] .…”