Circularly Polarized Luminescence Signals Research Articles

Dynamic Near‐Infrared Circularly Polarized Luminescence Encoded by Transient Supramolecular Chiral Assemblies

Circularly polarized luminescence (CPL) is promising for applications in many fields. However, most systems involving CPL are within the visible range; near‒infrared (NIR) CPL‒active materials, especially those that exhibit high glum values and can be controlled spatially and temporally, are rare. Herein, dynamic NIR‒CPL with a glum value of 2.5[[EQUATION]]10‒2 was achieved through supramolecular coassembly and energy transfer strategies. The chiral assemblies formed by the coassembly between adenosine triphosphate (ATP) and a pyrene derivative exhibit a red CPL signal (glum of 10‒3). The further introduction of sulfo‒cyanine5 resulted in a cooperative energy transfer process, which not only aroused the NIR CPL but also increased the glum value to 10‒2. Temporal control of these chiral assemblies was realized by introducing alkaline phosphatase to fabricate a biomimetic enzyme‒catalyzed network, allowing the dynamic NIR CPL signal to be turned on. Based on these enzyme‐regulated temporally controllable dynamic CPL‐active chiral assemblies, a multilevel information encryption system was further developed. Our work provides a pioneering example for constructing dynamic NIR CPL materials holding the ability to perform temporal control via the supramolecular assembly strategy, which is expected to aid in the design of supramolecular complex systems that more closely resemble natural biological systems.

Dynamic Near-Infrared Circularly Polarized Luminescence Encoded by Transient Supramolecular Chiral Assemblies.

Circularly polarized luminescence (CPL) is promising for applications in many fields. However, most systems involving CPL are within the visible range; near‒infrared (NIR) CPL‒active materials, especially those that exhibit high glum values and can be controlled spatially and temporally, are rare. Herein, dynamic NIR‒CPL with a glum value of 2.5[[EQUATION]]10‒2 was achieved through supramolecular coassembly and energy transfer strategies. The chiral assemblies formed by the coassembly between adenosine triphosphate (ATP) and a pyrene derivative exhibit a red CPL signal (glum of 10‒3). The further introduction of sulfo‒cyanine5 resulted in a cooperative energy transfer process, which not only aroused the NIR CPL but also increased the glum value to 10‒2. Temporal control of these chiral assemblies was realized by introducing alkaline phosphatase to fabricate a biomimetic enzyme‒catalyzed network, allowing the dynamic NIR CPL signal to be turned on. Based on these enzyme-regulated temporally controllable dynamic CPL-active chiral assemblies, a multilevel information encryption system was further developed. Our work provides a pioneering example for constructing dynamic NIR CPL materials holding the ability to perform temporal control via the supramolecular assembly strategy, which is expected to aid in the design of supramolecular complex systems that more closely resemble natural biological systems.

Achiral Solvent Inversed Helical Pathway and Cosolvent Controlled Excited-State "Majority Rule" in Enantiomeric Dansulfonamide Assemblies.

Achiral solvents are commonly utilized to induce the self-assembly of chiral molecules. This study demonstrates that achiral solvents can trigger helicity inversion in the assemblies of dansyl amphiphiles and control the excited-state "majority rule" in assemblies composed of pure enantiomers, through variation of the cosolvent ratio. Specifically, enantiomers of dansyl amphiphiles self-assemble into helical structures with opposite handedness in methanol (MeOH) and acetonitrile (MeCN), together with inversed circular dichroism and circularly polarized luminescence (CPL) signals. When a mixture of MeOH and MeCN is employed, the achiral cosolvents collectively affect the CPL of the assemblies in a way similar to that of "mixed enantiomers". The dominant cosolvent governs the CPL signal. As the cosolvent composition shifts from pure MeCN to MeOH, the CPL signals undergo a significant inversion and amplification, with two maxima observed at ≈20% MeOH and 20% MeCN. This study deepens the comprehension of how achiral solvents modulate helical nanostructures and their excited-state chiroptical properties.

Amplified Circularly Polarized Luminescence Behavior in Chiral Co-assembled Liquid Crystal Polymer Films via the Strategic Manipulation of Chiral Inducers.

One of the most important factors for the future application of circularly polarized luminescence (CPL) materials is their high dissymmetry factors (gem), and more and more studies are working tirelessly to focus on increasing the gem value. Herein, we chose an achiral liquid crystal polymer (LC-P) and two chiral binaphthyl-based inducers (R/S-3 and R/S-6) with different substitution positions (3,3' positions for R/S-3 and 6,6' positions for R/S-6) to construct chiral co-assemblies and explored their induced amplification CPL behaviors. Interestingly, after the thermal annealing treatment, this kind of chiral co-assembly (R/S-3)0.05-(LC-P)0.95 can emit a superior CPL signal (|gem| = 0.31 and λem = 424 nm), which achieves about 13-fold signal amplification in the spin-coated film, compared to (R/S-6)0.1-(LC-P)0.9 (|gem| = 0.023 and λem = 424 nm). This is because (R/S-3)0.05-(LC-P)0.95 could further co-assemble to form a more ordered arrangement LC state and generate regular helix nanofibers than that of (R/S-6)0.1-(LC-P)0.9. This work provides an efficient method for synthesizing high-quality CPL-active materials through the strategic manipulation of the structure of chiral binaphthyl-based inducers in chiral co-assembled LCP systems.

Unraveling the structure-chirality sensing relationship between achiral anthracene-based tetracationic nanotubes and nucleosides in aqueous host-guest complexation

In biological systems, nucleosides play crucial roles in various physiological processes. In this study, we designed and synthesized four achiral anthracene-based tetracationic nanotubes (1–4) as artificial hosts and chiroptical sensors for nucleosides in aqueous media. Notably, different nanotubes exhibit varied chirality sensing on circular dichroism (CD)/circularly polarized luminescence (CPL) spectra through the host-guest complexation, which prompted us to explore the factors influencing their chiroptical responses. Through systematic host-guest experiments, the structure-chirality sensing relationship between achiral anthracene-based tetracationic nanotubes and nucleosides in the host-guest complexation was unraveled. Firstly, the CD response originates from the anthracene rings situated at the side-wall position, resulting from the right-handed (P)- or left-handed (M)-twisted conformation of the macrocyclic structure. Secondly, the CPL signal is influenced by the presence of anthracene rings at the linking-wall position, which results from intermolecular chiral twisted stacking between these anthracene rings. Therefore, these nanotubes can serve as chiroptical sensor arrays to enhance the accuracy of nucleotide recognition through principal component analysis (PCA) analysis based on the diversified CD spectra. This study provides insights for the construction of adaptive chirality from achiral nanotubes with dynamic conformational nature and might facilitate further design of chiral functional materials for several applications.

Handedness-Inverted and Stimuli-Responsive Circularly Polarized Luminescent Nano/Micromaterials Through Pathway-Dependent Chiral Supramolecular Polymorphism.

The precise manipulation of supramolecular polymorphs has been widely applied to control the morphologies and functions of self-assemblies, but is rarely utilized for the fabrication of circularly polarized luminescence (CPL) materials with tailored properties. Here, this work reports that an amphiphilic naphthalene-histidine compound (NIHis) readily self-assembled into distinct chiral nanostructures through pathway-dependent supramolecular polymorphism, which shows opposite and multistimuli responsive CPL signals. Specifically, NIHis display assembly-induced CPL from the polymorphic keto tautomer, which become predominant during enol-keto tautomerization shifting controlled by a bulk solvent effect. Interestingly, chiral polymorphs of nanofiber and microbelt with inverted CPL signals can be prepared from the same NIHis monomer in exactly the same solvent compositions and concentrations by only changing the temperature. The tunable CPL performance of the solid microbelts is realized under multi external physical or chemical stimuli including grinding, acid fuming, and heating. In particular, an emission color and CPL on-off switch based on the microbelt polymorph by reversible heating-cooling protocol is developed. This work brings a new approach for developing smart CPL materials via supramolecular polymorphism engineering.

Cholesterol-decorated porphyrin with circularly polarized luminescence: Design, synthesis and properties

Porphyrin was an excellent near-infrared dye but its rigid planar structure is not favorable for producing circularly polarized luminescence (CPL) property. Chirality transfer is an effective strategy to realize the CPL emission for achiral fluorescent unit. In this study, porphyrin derivatives with four cholesterol groups and dodecyl groups B4C and B4D were designed and synthesized. B4C and B4D exhibited good near-infrared emission in both solution and aggregated states. The solid film of B4C emitted strong left CPL fluorescence, while this CPL signal in mesomorphic film was stronger and switched to right CPL emission. The fluorescence dissymmetry factor (glum) of B4C was as high as 2.31×10−2. These results suggested the effective chirality transfer from cholesterol units to porphyrin units based on spiral columnar liquid crystalline stacking and the CPL signal of B4C was tunable by temperature, supplying a good way on design and synthesis of CPL material with tunable CPL signal based on achiral dyes.

Efficient Circularly Polarized Luminescence and Bright White Emission from Hybrid Indium‐Based Perovskites via Achiral Building Blocks

AbstractChiral organic‐inorganic hybrid perovskites (OIHPs) exhibit exceptional optical and chiral properties, demonstrating potential for 3D display, circularly polarized light‐emitting diodes (CP‐LEDs), and CPL switches. However, the construction of chiral OIHPs often relies on chiral building blocks, limiting chemical diversity, and possessing challenges in achieving large asymmetry factor (glum) without sacrificing photoluminescence quantum yield (PLQY). Here, Chiral DMA4In1‐xSbxCl7 (DMA = dimethylammonium, x = 0 to 1) with superior circularly polarized luminescence (CPL) are successfully constructed based on achiral building blocks DMA+ and metal halides. By optimizing the Sb3+ content, bright white emission with a high PLQY of 69.13% is achieved, as well as near‐unity PLQY yellow emission and strong CPL signals with a glum of up to +1.40 × 10−2, exhibiting a performance comparable to state‐of‐the‐art chiral OIHPs. Combining optical characterizations and theoretical calculations reveal that these intriguing properties originate from the intrinsic chiral helical structures and a pair of perfect complementary color emissions in DMA4In1‐xSbxCl7. In addition, DMA4In1‐xSbxCl7 exhibit excellent thermal stability and mild thermal quenching in the temperature range of 300 to 420 K. These fascinating properties suggest that DMA4In1‐xSbxCl7 have significant applications in white light‐emitting diodes (WLED), 3D displays and anti‐counterfeiting.

Strong Circularly Polarized Luminescence Promoted by AIE-active Chiral Co-assemblies in Liquid Crystal Polymer Films.

Recently, extensive works have focused on increasing the dissymmetry factors (glum ) of various circularly polarized luminescence (CPL) materials, which is one of the most important factors for future applications of CPL. Herein, we designed a chiral co-assembled liquid crystal polymer (LCP) PTZ@R/S-PB2, which was prepared by chiral binary co-polymer (R/S-PB2) doped with achiral phenothiazine derivation dye (PTZ). For comparison, ternary co-polymerized LCP (R/S-PT) was synthesized by co-polymerizing with mesogenic monomer, chiral monomer and emissive monomer. Both PTZ@R/S-PB2 and R/S-PT showed aggregation-induced emission (AIE) properties. Interestingly, the CPL signals of both PTZ@R/S-PB2 and R/S-PT were reversed and amplified after thermal annealing treatment. The |glum | values of the co-assembled PTZ@R/S-PB2 were up to 0.13 at a 32 nm thickness, which was 5.4 times that of R/S-PT (|glum |=0.024). This is due to PTZ@R/S-PB2 could form more orderly chiral co-assembly structures. Noticeably, increasing the LCP film thickness could further improve the glum value, and the maximum glum of PTZ@R/S-PB2 could be enhanced to +0.91/-0.82 at a 220 nm thickness.

Light-Driven Sign Inversion of Circularly Polarized Luminescence Enabled by Dichroism Modulation in Cholesteric Liquid Crystals.

Stimuli-responsive circularly polarized luminescence (CPL) materials show great promise in applying information encryption and anticounterfeiting. Herein, light-driven CPL sign inversion is achieved by combining a photoresponsive achiral negative dichroic dye (KG) and a static achiral positive dichroic dye (NR) as dopants at the 0.5:0.5 weight ratio into the cholesteric liquid crystal (CLC) host. The side chains of KG undergo trans/cis isomerization after 365nm UV light irradiation, leading to the dichroism (SF ) decrease. The |glum | value of CLC doping with KG (CLC-KG) weakens from 0.67 to 0.28 in response to the order degree change. Taking advantage of its unique CPL response property, the light-driven CPL sign inversion is achieved (from -0.20/0.14 to 0.02/-0.04) by incorporating NR (0.5:0.5) into the CLC-KG with helical superstructure static. Based on the synergistic use of circular polarization and responsiveness state as cryptographic primitives, the multidimensional information encryption CLC system can be realized.

Circularly polarized luminescence from a common alkoxy pillar[5]arene and its co‐aggregates with π‐conjugated rods

AbstractCylinder‐shaped macrocycles composed of π‐panels have attracted special attention as one of the best platforms for the development of organic molecule‐based chiroptical materials. Pillar[n]arenes are a class of macrocycles with the advantage of easy preparation but have not been extensively investigated from the perspective of luminescent molecules. However, common alkoxy pillar[n]arenes are fluorescent in non‐haloalkane solvents, showing potential to be used for molecule‐based chiroptical materials. In this work, circularly polarized luminescence (CPL) spectra are reported for a pillar[5]arene with stable planar chirality using tetrahydrofuran (THF) and cyclohexane as solvents, which has been missing for many years. The pillar[5]arene also forms co‐aggregates with 1,4‐bis(phenylethynyl)benzene and 1,4‐bis[(pentafluorophenyl)ethynyl]benzene in THF/H2O mixtures, owing to a hydrophobic effect. The co‐aggregates with the fluorinated π‐rod display a new low‐energy absorption peak and broad emission band as well as intense circular dichroism and CPL signals. Chiral information from the enantiopure pillar[5]arene core is efficiently transmitted to the co‐aggregates with the π‐conjugated rod, leading to the highest dissymmetry factor for CPL (2.9 × 10−2 at 472 nm) among pillar[n]arene‐based CPL materials.

Aqueous Circularly Polarized Luminescence Induced by Homopolypeptide Self-Assembly.

Remarkable advances have been achieved in solution self-assembly of polypeptides from the perspective of nanostructures, mechanisms, and applications. Despite the intrinsic chirality of polypeptides, the promising generation of aqueous circularly polarized luminescence (CPL) based on their self-assembly has been rarely reported due to the weak fluorescence of most polypeptides and the indeterminate self-assembly mechanism. Here, we propose a facile strategy for achieving aqueous CPL based on the self-assembly of simple homopolypeptides modified with a terminal group featuring both twisted intramolecular charge transfer and aggregation-induced emission properties. A morphology-dependent CPL can be observed under different self-assembly conditions by altering the solvents. A nanotoroid-dispersed aqueous solution with detectable CPL can be obtained by using tetrahydrofuran as a good solvent for the self-assembly, which is attributed to the involvement of the terminal group in the chiral environment formed by the homopolypeptide chains. However, such a chiral packing mode cannot be realized in nanorods self-assembled from dioxane, resulting in an inactive CPL phenomenon. Furthermore, CPL signals can be greatly amplified by co-assembly of homopolypeptides with the achiral small molecule derived from the terminal group. This work not only provides a pathway to construct aqueous CPL-active homopolypeptide nanomaterials but also reveals a potential mechanism in the self-assembly for chiral production, transfer, and amplification in polypeptide-based nanostructures.

A Single-Enantiomer Emitter Enabled Superstructural Helix Inversion for Upconverting and Downshifting Luminescence with Bidirectional Circular Polarization.

The helical twisting tendency of liquid crystals (LCs) is generally governed by the inherent configuration of the chiral emitter. Here, we introduce the multistage inversion of supramolecular chirality as well as circularly polarized luminescence (CPL) by manipulating the ratio of single enantiomeric emitters (R-PCP) to LC monomers (5CB). Increasing the content of R-PCP from 1 wt % to 3 wt % inverted the helix of LCs from left-handed to right-handed, accompanying a CPL sign changed from positive to negative. The biaxiality of chiral emitters, as well as the steric effect of chiral-chiral and chiral-achiral interaction, were identified as the reasons for helical sense inversion. Due to the strong helical twisting power, 4 wt % R-PCP drove the photonic band gap (PBG) of chiral LCs to match up with their emission range, leading to an inversion of the CPL again with a high dissymmetry factor (≈1.2). Directly adjusting the PBG using chiral emitters is seldom achieved in cholesteric LCs. On this basis, an achiral sensitizer PtTPBP was assembled into the helical superstructure. The generation of triplet-triplet annihilation-induced upconverted CPL from R-PCP and the downshifting CPL from PtTPBP with opposite rotation was achieved in a single chiral LC system by tuning the position of the PBG.

Clustering-Triggered Emission Liquid Crystalline Polymer Bearing Cholesterol: Tunable Circularly Polarized Luminescence and Room-Temperature Phosphorescence.

Circularly polarized luminescence (CPL) materials with clustering-triggered emission (CTE) characteristic have gradually attracted attention for their unique photophysical properties. However, the majority of reported clusteroluminogens lack chirality and exhibit heterogeneity, making it challenging to achieve a well-defined helical structure necessary for efficient CPL with high dissymmetry factor (glum ). In this paper, chiral liquid crystals are constructed to obtain CTE-based CPL materials with high glum values. Side chain liquid crystal polymer PM6Chol bearing cholesterol clusteroluminogens are designed and synthesized. PM6Chol-coated film and PM6Chol thermal-treated film are also successfully prepared by different film-forming methods. Both the films inherit the CTE characteristic of cholesterol and show excitation wavelength-dependent luminescent behavior. However, the two polymer films exhibit different liquid crystal phase structures, with PM6Chol-coated film being a chiral bilayer smectic C phase and PM6Chol thermal-treated film being an achiral bilayer smectic A phase. Attributed to helical arrangement of cholesterol, PM6Chol-coated film emits efficient CPL with glum values up to 1.0 × 10-1 . For PM6Chol thermal-treated film, no CPL signal is detected due to the absence of helical structure. However, it shows obvious room-temperature phosphorescence with 2.0 s afterglow and 23.9ms lifetime.

Achiral Dichroic Dyes-mediated Circularly Polarized Emission Regulated by Orientational Order Parameter through Cholesteric Liquid Crystals.

It is noteworthy that cholesteric liquid crystal (CLC) platforms have been witnessed in high-performance circularly polarized luminescence (CPL) behaviors through the highly organized chiral co-assembled arrangement of achiral dyes. However, most CPL-active design strategies are closely relative to the helix co-assembly structure of CLC rather than achiral dyes. Herein, we developed an intriguing regulation strategy for CPL-active CLC materials. They were regulated using the orientational order parameter (SF) of achiral dichroic dyes as an incisive probe for the order arrangement degree of achiral dyes in CLC media. The I-shaped phenothiazine derivative PHECN dye (SF =0.30) emitted a strong CPL signal (|glum| = 0.47). In contrast, the T-shaped derivative (PHEBen) dye (SF =0.09) showed a weak circular polarization level (|glum| = 0.07) at similar CLC textures. Most interestingly, this kind of dichroic PHECN dye with a higher SF could greatly improve the contrast ratio of CPL (Δglum = 0.47) and emission intensity (ΔFL = 46.0%) at direct-current electric field compared with the T-shaped PHEBen (Δglum = 0.07 and ΔFL = 1.0%) in CLCs. This work demonstrates that an induced CPL emission can be mediated using achiral dichroic dye, which will open a new avenue for developing excellent CPL-active display materials.

Achiral Dichroic Dyes‐mediated Circularly Polarized Emission Regulated by Orientational Order Parameter through Cholesteric Liquid Crystals

AbstractIt is noteworthy that cholesteric liquid crystal (CLC) platforms have been witnessed in high‐performance circularly polarized luminescence (CPL) behaviors through the highly organized chiral co‐assembled arrangement of achiral dyes. However, most CPL‐active design strategies are closely relative to the helix co‐assembly structure of CLC rather than achiral dyes. Herein, we developed an intriguing regulation strategy for CPL‐active CLC materials. They were regulated using the orientational order parameter (SF) of achiral dichroic dyes as an incisive probe for the order arrangement degree of achiral dyes in CLC media. The I‐shaped phenothiazine derivative PHECN dye (SF=0.30) emitted a strong CPL signal (|glum|=0.47). In contrast, the T‐shaped derivative (PHEBen) dye (SF=0.09) showed a weak circular polarization level (|glum|=0.07) at similar CLC textures. Most interestingly, this kind of dichroic PHECN dye with a higher SF could greatly improve the contrast ratio of CPL (Δglum=0.47) and emission intensity (ΔFL=46.0 %) at direct‐current electric field compared with the T‐shaped PHEBen (Δglum=0.07 and ΔFL=1.0 %) in CLC. This work demonstrates that an induced CPL emission can be mediated using achiral dichroic dye, which will open a new avenue for developing excellent CPL‐active display materials.

Inverted circularly polarized luminescence based on self-assembly of (1S)-camphanic-decorated biscyanostilbene in smectic mesophase and suspension

The regulation of circularly polarized luminescence (CPL) signal is of great significance for practical application but rarely reported. In this work, the sign inversion of CPL based on assemblies in smectic mesophase and suspension was developed. Two stable conformers of (1S)-camphanic-decorated biscyanostilbene accounted for the formation of two different helical superstructures. Smectic mesophase was found to be a bilayer structure consisted of cis-like conformer and emitted right-handed CPL with a glum of −0.019, while chiral assembly in suspension was made up of trans-like conformer and exhibited left-handed CPL with a glum of 0.018. This research supplied a new strategy to tune the inverted CPL signal of homogeneous organic molecular system by simple external condition control.

Single Molecular Persistent Room-Temperature Phosphorescence and Circularly Polarized Luminescence from Binaphthol-Decorated Optically Innocent Cyclotriphosphazenes.

Circularly polarized luminescence (CPL) features of BINOL-decorated cyclotriphosphazenes (CPs) are reported for the first time. The luminescence dissymmetry factor (glum ) of these compounds in chloroform solutions and polymethyl methacrylate (PMMA) thin films with wt 1 % doping concentrations are found to be 1.0×10-3 , and 2.9×10-3 , respectively. However, no CPL signal is observed for the pristine solids. The enantiomers (CP-(R)/CP-(S)) show ultraviolet photoluminescence (~350-360 nm) in solution and the solid state. These compounds show ~10 times larger absolute photoluminescence quantum yield (PLQY) than the simple BINOLs in the solutions state. In the solid state, CP-(R) shows larger PLQY than binaphthol-(R); in contrast, the S enantiomer shows lower PLQY than binaphthol-(S); this indicates that the isomer-dependent solid-state packing of these compounds plays a crucial role in controlling the PL. Thin films with more than 1 % doping concentration and pristine solids of these compounds do not show persistent room-temperature phosphorescence (pRTP) due to concentration-caused quenching. However, thin films with wt 1 % of these chiral emitters exhibit pRTP characteristics with a ~159-343 ms lifetime under vacuum. Theoretical calculations reveal that the cyclophosphazene acts as an optically innocent dendritic core, and the optical features of these compounds are dictated by the pendent BINOL chromophore.

A Photo‐ and Thermo‐Driven Azoarene‐Based Circularly Polarized Luminescence Molecular Switch in a Liquid Crystal Host

AbstractThe development of chiral optical active materials with switchable circularly polarized luminescence (CPL) signals remains a challenge. Here an azoarene‐based circularly polarized luminescence molecular switch, (S, R, S)‐switch 1 and (R, R, R)‐switch 2, are designed and prepared with an (R)‐binaphthyl azo group as a chiral photosensitive moiety and two (S)‐ or (R)‐binaphthyl fluorescent molecules with opposite or the same handedness as chiral fluorescent moieties. Both switches exhibit reversible trans/cis isomerization when irradiated by 365 nm UV light and 520 nm green light in solvent and liquid crystal (LC) media. In contrast with the control (R, R, R)‐switch 2, when switch 1 is doped into nematic LCs, polarization inversion and switching‐off of the CPL signals are achieved in the resultant helical superstructure upon irradiation with 365 nm UV and 520 nm green light, respectively. Meanwhile, the fluorescence intensity of the system is basically unchanged during this switching process. In particular, these variations of the CPL signals could be recovered after heating, realizing the true sense of CPL reversible switching. Taking advantage of the unique CPL switching, the proof‐of‐concept for “a dual‐optical information encryption system” based on the above CPL active material is demonstrated.

A Photo- and Thermo-Driven Azoarene-Based Circularly Polarized Luminescence Molecular Switch in a Liquid Crystal Host.

The development of chiral optical active materials with switchable circularly polarized luminescence (CPL) signals remains a challenge. Here an azoarene-based circularly polarized luminescence molecular switch, (S, R, S)-switch 1 and (R, R, R)-switch 2, are designed and prepared with an (R)-binaphthyl azo group as a chiral photosensitive moiety and two (S)- or (R)-binaphthyl fluorescent molecules with opposite or the same handedness as chiral fluorescent moieties. Both switches exhibit reversible trans/cis isomerization when irradiated by 365 nm UV light and 520 nm green light in solvent and liquid crystal (LC) media. In contrast with the control (R, R, R)-switch 2, when switch 1 is doped into nematic LCs, polarization inversion and switching-off of the CPL signals are achieved in the resultant helical superstructure upon irradiation with 365 nm UV and 520 nm green light, respectively. Meanwhile, the fluorescence intensity of the system is basically unchanged during this switching process. In particular, these variations of the CPL signals could be recovered after heating, realizing the true sense of CPL reversible switching. Taking advantage of the unique CPL switching, the proof-of-concept for "a dual-optical information encryption system" based on the above CPL active material is demonstrated.