Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

Abstract

Because of their unique structural and optical properties, 1D perylene diimide (PDI) derivatives have gained attention for use in optoelectronic devices. However, PDI‐containing self‐assembled supramolecular systems often are of limited use because they have supramolecular architectures that are held together by weak noncovalent π–π stacking, hydrogen bonding, and hydrophobic interactions. As a result, they are intrinsically unstable under solution‐processing conditions. To overcome this limitation, a polydiacetylene (PDA)‐based strategy is developed to construct a solvent‐resistant and stable PDI assembly. For this purpose, first the monomer PDI–BisDA is generated, in which two polymerizable diacetylene (DA) units are covalently linked to a PDI core. Importantly, 254 nm UV irradiation of self‐assembled PDI–BisDA nanofibers forms solvent‐resistant and stable PDI–PDA fibers. Owing to the presence of PDA, the generated polymer fibers display an increased photocurrent. In addition, the existence of PDA and PDI moieties in the fiber leads to the occurrence of switchable on–off fluorescence resonance energy transfer (FRET) between the PDI and reversibly thermochromic PDA chromophores.

Highly Sensitive Polydiacetylene Ensembles for Biosensing and Bioimaging

“…In recent years, the preparation methods for PDA have been greatly advanced. PDA structures have been enriched from traditional films, micelles and vesicles to 3D-PDA structures, porous structures, hydrogels, macrocyclic structures, and single-layer nanosheets (Bang et al, 2016;Chae et al, 2016;Krishnan et al, 2016;Okaniwa et al, 2016;Jordan et al, 2017;Li et al, 2017a;Romera et al, 2017;Jeong et al, 2018;Takeuchi et al, 2018;Terada et al, 2018;Heo et al, 2019;Hu et al, 2019;Seo et al, 2019;Shin et al, 2020). Great progresses have also been made in the preparation of reversible and chiral PDA (Chen et al, 2016;He et al, 2020).…”

Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

“…[ 39 ] However, following polymerization of the diacetylene sidechains by UV irradiation, the fluorescence emitted by the film was almost completely quenched (Figure 2A, black spectrum), likely accounting for energy transfer from the anthraquinone units to the PDA network resulting in effective energy dissipation. [ 28 ]…”

“…[ 23–26 ] Diacetylenes displaying aromatic headgroups have attracted interest in recent years due to the distinctive morphologies, optical, and electronic properties of the polymerized systems. [ 24,27–29 ]…”

Chromatic response of cationic polydiacetylene vesicles induced by permeation of target compound

“…Generally, PDA exhibits a color change from blue to red upon external stimulus and over the past decade, many papers reporting PDAs applied to sensors have been published. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] A representative method to form the sensing system using PDA is vesicle formation. The PDA vesicle solution is easily formed by sonication of the amphiphilic diacetylene compound in water.…”