Due to the characteristics of optical rotation, selective emission of polarized light, and circular dichroism, circularly polarized luminescent materials have aroused extensive attentions, and they have exhibited wide optoelectronic applications, such as optical data storage, liquid crystal display, and backlights in 3D displays. Here, the research progress of circularly polarized luminescent materials for organic optoelectronic devices is summarized. First, the definition and measurement of the circularly polarized light, such as optical rotatory dispersion, circular dichroism, and circularly polarized luminescence, are systematically introduced. Subsequently, the design strategies for various kinds of circularly polarized luminescent materials, including luminescent lanthanide and transition‐metal complexes, small organic luminophores, conjugated polymers, supramolecules, and liquid crystals are summarized. These materials exhibit circularly polarized luminescence with different magnitudes of luminescence dissymmetry values (glum). They are further applied in optoelectronic devices with excellent performance, and the influence factors on the glum values of these materials are presented in detail. Finally, the current opportunities and challenges in this rapidly growing research field are discussed systematically. The circularly polarized luminescent materials with large glum and high luminescence efficiency are very promising for applications in organic optoelectronic fields.

Recent Progress on Circularly Polarized Luminescent Materials for Organic Optoelectronic Devices

Innovative technologies are highly pursued for the detection and avoidance of counterfeiting in modern information society. Herein, we report the construction of photo-responsive supramolecular polymers toward fluorescent anti-counterfeit applications, by taking advantage of multicycle anthracene‒endoperoxide switching properties. Due to σ-metalation effect, photo-oxygenation of anthracene to endoperoxide is proceeded under the mild visible light irradiation conditions, while the backward conversion occurs spontaneously at room temperature. Supramolecular polymers are formed with cooperative nucleation‒elongation mechanism, which facilitate fluorescence resonance energy transfer process via two-component co-assembly strategy. Fluorescence resonance energy transfer efficiency is delicately regulated by either light-triggered anthracene‒endoperoxide conversion or vapor-induced monomer-polymer transition, leading to high-contrast fluorescent changes among three different states. On this basis, dual-mode anti-counterfeiting patterns have been successfully fabricated via inkjet printing techniques. Hence, cooperative supramolecular polymerization of photo-fluorochromic molecules represents an efficient approach toward high-performance anti-counterfeit materials with enhanced security reliability, fast response, and ease of operation.

/pdf/cooperative-supramolecular-polymers-with-anthracene-3j2nsvm4xn.pdf

Cooperative supramolecular polymers with anthracene‒endoperoxide photo-switching for fluorescent anti-counterfeiting

Modern functional adhesives have attracted considerable attention due to their reversible adhesion capacities and stimuli-responsive adhesion behavior. However, for modern functional adhesives, polymeric structures were highly necessary to realize adhesion behaviors. Supramolecular adhesives from low-molecular-weight monomers were rarely recognized. Compared with polymeric adhesive materials, it remains challenging for supramolecualr adhesive materials to realize tough adhesion on wet surfaces or even under water. In this study, a new supramolecular adhesive consisting of low-molecular-weight monomers was successfully designed and prepared. Strong and long-term adhesion performance was realized on various surfaces, with a maximum adhesion strength of 4.174 MPa. This supramolecular adhesive exhibits tough and stable adhesion properties in high-moisture and underwater environments (including seawater). Long-term underwater adhesion tests display the potential application of low-molecular-weight adhesive as a marine adhesive.

Tough, Long-Term, Water-Resistant, and Underwater Adhesion of Low-Molecular-Weight Supramolecular Adhesives.

Supramolecular polymers based on host-guest molecular recognition have emerged as promising platforms for the development of smart materials. However, the studies on them are primarily conducted in solution and/or in the gel state. In contrast, little is known about dynamic properties and applications of supramolecular polymers in bulk. Herein, we present a self-cross-linking supramolecular polymer network (SPN) as a model system to understand the bulk properties controlled by noncovalent interactions. Specifically, the SPN monomer is composed of two benzo-21-crown-7 (B21C7) host units and two dialkylammonium salt guest moieties on a four-arm core, wherein complementary host-guest complexation drives the formation of the SPN with [2]pseudorotaxane linkages between B21C7 and ammonium motifs. The dynamic and reversible behaviors of the linkages are evaluated by measurement of viscoelasticity. The results indicate that the host-guest molecular recognition becomes highly dynamic at elevated temperature. Moreover, the relatively high activation energy of the SPN manifests itself as a new type of thermoplastic material with network topology freezing glass transition. Finally, we demonstrate how these findings provide insights into the malleability and processability of the SPN by simple demos. The fundamental understanding gained from the research on this SPN in bulk will facilitate the advancement and application of supramolecular materials.

A Self-Cross-Linking Supramolecular Polymer Network Enabled by Crown-Ether-Based Molecular Recognition.

Supramolecular polymers fabricated by orthogonal self-assembly based on multiple hydrogen bonding and macrocyclic host–guest interactions

One-dimensional organic structures with well-oriented π-aggregation, strong emission, and ease of processability are desirable for optoelectronic waveguiding devices. Herein, we have developed an unprecedented strategy to attain this objective, by self-assembling platinum(II) acetylides into fluorescent supramolecular polymers via cooperative mechanism. The resulting high-molecular-weight supramolecular polymers are capable of forming electrospun microfibers with uniform geometry and smooth surface, which enable light propagation with extremely low scattering loss (0.008 dB μm-1). With the elaborate combination of bottom-up supramolecular polymerization and top-down electrospinning techniques, this work offers a novel and versatile avenue toward high-performance optical waveguiding materials.

Cooperative Supramolecular Polymerization of Fluorescent Platinum Acetylides for Optical Waveguide Applications

Conjugated polymers (CPs) with deep LUMO energy levels (ELUMOs) are essential for developing n-type organic electronics. However, few approaches can markedly lower the ELUMOs of CPs. Herein, this issue is addressed by the introduction of a quinoidal building block into the polymer chain. Two CPs, PIQ-A and PIQ-O, are synthesized based on an indandione-terminated quinoidal unit, with alkyl or oligo(ethylene glycol) side chains on the comonomer, respectively. The CPs show ultralow ELUMOs of ca. −4.30 eV, which is lower by 0.75 eV compared to the analogous polymer with aromatic conjugated structure. The deep LUMO energy levels endow the CPs with unipolar n-type transport behavior in organic thin-film transistors and efficient n-type doping in organic thermoelectrics, with doped PIQ-O showing an optimized electrical conductivity of 0.43 S cm–1 and a power factor of 4.24 μW m–1 K–2. Importantly, the electrical conductivity of doped polymer thin films (∼50 nm) barely changes after a 7 day exposure to air, and the doped PIQ-O film shows an electrical conductivity of 0.39 S cm–1 even after a 15 day exposure to air. This work provides a new approach to develop CPs with ultralow LUMO energy levels, toward high-performance and potentially air-stable n-type organic electronics. 

n-Type Conjugated Polymers Based on an Indandione-Terminated Quinoidal Building Block

Selective doping of a single conjugated polymer (CP) to obtain p‐type and n‐type conductive materials would be highly attractive for organic thermoelectric applications, because it will greatly reduce the time and costs of synthesizing different types of CPs. However, this strategy has rarely been investigated. In this study, two CPs are synthesized, designated PTQDPP‐T and PTQDPP‐2FT, based on a newly developed quinoidal unit with thienoisatin as the termini and a thiophene‐flanked diketopyrrolopyrrole (ThDPP) unit as the quinoidal core. The electron‐rich thiophene rings in thienoisatin and the electron delocalization induced by thienoisatin resulted in polymers with high‐lying highest occupied molecular orbital, and the electron‐deficient nature of ThDPP unit and its quinoidal backbone endowed the polymers with low‐lying lowest unoccupied molecular orbitals. As a result, both polymers can be p‐type and n‐type doped. Because of its high mobility, doped PTQDPP‐2FT performed better in organic thermoelectric devices than the doped PTQDPP‐T. After being doped with FeCl3 and N‐DMBI, PTQDPP‐2FT showed p‐type and n‐type power factors of 278.2 and 2.37 µW m−1 K−2, respectively. These are the best for bipolar (p‐type and n‐type) performances that obtained by selective doping of a single polymer.

Realizing p‐Type and n‐Type Doping of a Single Conjugated Polymer via Incorporation of a Thienoisatin‐Terminated Quinoidal Unit

Enhanced n‐type thermoelectric performance of conjugated polymers based on an indandione‐terminated quinoidal unit through comonomer optimization

A series of aromatic polyesters were prepared by the reaction of bisphenol-A and bis(hydroxyphenyl)butane with diacyl chloride monomers by phase transfer interfacial polycondensation in order to improve the processability of the bisphenol A-based polyarylate. The microstructure, molecular weight, crystallinity, solubility, thermal properties, mechanical properties, and optical properties of the prepared copolyesters were investigated. Inherent viscosities of the copolyesters are in the range of 0.14–0.53 dl g−1, and their average molecular weights are 7362–44,413 g mol−1, respectively. The feed compositions and copolymer compositions were nearly identical. The results show that with the increase in the content of side ethyl units, the copolyester gradually transforms into an amorphous structure, which is also verified by the improvement in dissolution properties. When the copolyester backbone was introduced into the side ethyl units, the thermal decomposition temperature was less affected and varied in the range of about 10°C, while the value of glass transition temperature reduced from 196.5°C to 165.1°C. The mechanical properties of the polymers are similar to those of the industrial commodity U-100. In addition, the copolyester films have good optical properties, and the transmittance reached the maximum value of 98.41% when the content of bis(hydroxyphenyl)-butane was 10%. 

Synthesis of aromatic polyesters derived from bisphenol‐A and bis(hydroxyphenyl)butane with diacyl chloride monomers

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