Efficient Photosensitizers Research Articles

Design of AsLOV2 domain as a carrier of light-induced dissociable FMN photosensitizer.

Flavin mononucleotide (FMN) is a highly efficient photosensitizer (PS) yielding singlet oxygen (1 O2 ). However, its 1 O2 production efficiency significantly decreases upon isoalloxazine ring encapsulation into the protein matrix in genetically encoded photosensitizers (GEPS). Reducing isoalloxazine ring interactions with surrounding amino acids by protein engineering may increase 1 O2 production efficiency GEPS, but at the same time weakened native FMN-protein interactions may cause undesirable FMN dissociation. Here, in contrast, we intentionally induce the FMN release by light-triggered sulfur oxidation of strategically placed cysteines (oxidation-prone amino acids) in the isoalloxazine-binding site due to significantly increased volume of the cysteinyl side residue(s). As a proof of concept, in three variants of the LOV2 domain of Avena sativa (AsLOV2), namely V416C, T418C, and V416C/T418C, the effective 1 O2 production strongly correlated with the efficiency of irradiation-induced FMN dissociation (wild type (WT) < V416C < T418C < V416C/T418C). This alternative approach enables us: (i) to overcome the low 1 O2 production efficiency of flavin-based GEPSs without affecting native isoalloxazine ring-protein interactions and (ii) to utilize AsLOV2, due to its inherent binding propensity to FMN, as a PS vehicle, which is released at a target by light irradiation.

Nature and energetics of low-lying excited singlets/triplets and intersystem crossing rates in selone analogs of perylenediimide: A theoretical perspective.

The structural rigidity and chemical diversity of the highly fluorescent perylenediimide (PDI) provide wide opportunities for developing triplet photosensitizers with sufficiently increased energy efficiency. Remarkably high intersystem crossing (ISC) rates with a complete fluorescence turn-off reported recently for several thione analogs of PDI due to substantially large spin-orbit coupling garners huge attention to develop other potential analogs. Here, several selone analogs of PDI, denoted as mSe-PDIs (m = 1-4) with varied Se content and positions, are investigated to provide a comprehensive and comparative picture down the group-16 using density functional theory (DFT) and time-dependent DFT implementing optimally tuned range-separated hybrid in toluene dielectric. All mSe-PDIs are confirmed to be dynamically stable and also thermodynamically feasible to synthesize from their oxygen and thione congeners. The first excited-state singlet (S1) of mSe-PDI with relatively low Se-content (m = 1, 2) is of nπ* character with an expected fluorescence turn-off. Whereas, the ππ* nature of the S1 for 3Se-PDI and 4Se-PDI suggests a possible fluorescence turn-on in the absence of any other active nonradiative deactivation pathways. However, ∼4-6 orders greater ISC rates (∼1012-1014 s-1) than the fluorescence ones (∼108 s-1) for all mSe-PDIs signify highly efficient triplet harvest. Importantly, significantly higher ISC rates for these mSe-PDIs than their thione congeners render them efficient triplet photosensitizers.

Fabrication and characterization of dissolving microneedles for transdermal delivery of hypocrellin A

Hypocrellin A (HA) is an efficient photosensitizer for photodynamic therapy in recent years. In order to improve the delivery of this photosensitizer, dissolving HA microneedles were established. Firstly, dissolving microneedles were prepared from HA by a two-step solvent casting method. Then, the dissolving HA microneedle were characterized by stereomicroscope, laser confocal microscope, scanning electron microscope, differential scanning calorimeter (DSC), X-ray diffractometer (XRD) and fourier infrared spectrometer (FTIR). Finally, the transdermal cumulative penetration experiments were conducted. The results showed that the dissolving HA microneedle has a conical shape with an average height of 650 μm. The mechanical strength endure a force of 44.78 N, resulting in 0.20 N per needle. The in vitro transdermal experiment showed that the dissolving HA microneedle almost completely dissolved in 5 min after insertion into the mouse skin. The depth of drug penetration through the skin can reach 601.36 μm. Moreover, the dissolving HA microneedle significantly improved the cumulative transdermal penetration efficiency of the photosensitizer through the skin. Therefore, the present study successfully established a dissolving microneedle of HA, which can quickly dissolve and significantly improve the transdermal delivery efficiency of HA.

Helical BODIPY Dyes as Heavy-Atom-Free Triplet Photosensitizers for Photodynamic Therapy of Cancer.

Despite of having many advantages over the popular cancer therapies, photodynamic therapy still is not widely acceptable for clinical applications. Scarcity of efficient triplet photosensitizers (PSs) is one of the main bottlenecks for this. Although numerous heavy atom attached PSs are developed as PDT agents, but these are not suitable for clinical applications due to several reasons. Thus, development of heavy-atom-free organic PSs is urgently required. In this context, development of new type of helical BODIPYs as PSs for PDT is discussed. BODIPYs have rich photophysical properties and structural helicity further enhances their triplet conversion rates. This new concept of structural helicity to enhance the triplet conversion of BODIPYs is discussed with reported helical BODIPYs. Helical geometries of these dyes are checked by X-ray crystallography studies and their high triplet conversions as compared to planar BODIPYs are also confirmed. Importantly, these dyes have high triplet lifetimes and are capable of generating high singlet oxygens even in hypoxia condition as compared to conventional heavy atom attached BODIPYs. All these make the helical BODIPYs excellent candidates as PDT agents. Finally, their successful applications as PDT agents in killing of various types of cancer cells are also discussed. The results are encouraging which indicate that helical BODIPYs could be next generation heavy-atom-free PSs for PDT applications.

Improved photocatalytic disinfection performance of graphitic carbon nitride through hybridization with humic acid /zinc peroxide: A synergistic generation of antimicrobial reactive oxygen species

Photocatalytic disinfection of bacteria using photosensitive nanomaterials is an efficient method for bacteria inactivation and is considered a beneficial alternative to chemical disinfectants that produce harmful by-products. However, due to the limited application scope of photocatalysts, the antibacterial efficiency remains unsatisfactory. To enhance the photocatalytic efficiency of the non-metal photosensitizer, graphitic carbon nitride (g-C3N4) nanosheets, they were composited with a metal-based photosensitizer, zinc peroxide (ZnO2) nanoparticles, with the aim of humic acid (HA). Besides the self-generating ability of H2O2 by ZnO2 in an aqueous medium, its deposition over g-C3N4 nanosheets enhances visible light harvesting and increases both surface area and active sites, thereby enhancing photocatalytic efficiency. The resulting composite, g-C3N4/ZnO2, produced more H2O2, •OH, and O2•- radicals than either component when exposed to visible light. Moreover, the photocatalyst demonstrated enhanced photocatalytic disinfection efficacy against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) under dark conditions compared to pure g-C3N4 nanosheets. However, a notably greater antibacterial activity was observed when the nanocomposites were subjected to light irradiation. FESEM images and live-dead assays revealed the physical contact of the nanocomposite with the surface of bacterial cells and the loss of cell membrane integrity. Furthermore, it was observed that there was greater cellular uptake of nanocomposites into cells and the generation of reactive oxygen species (ROS) under light irradiation compared to similar conditions in the dark, leading to an increased photoinactivation rate of bacteria. The enhanced photocatalytic and antibacterial activities of g-C3N4/ZnO2 nanocomposites make them attractive for a range of applications, including use in nanomedicine and environmental surface disinfection.

An Indacenodithieno[3,2‐b]thiophene‐based Organic Dye for P‐type Dye‐Sensitized Solar Cells and Photoelectrochemical H2O2 Production

AbstractEfficient photosensitizers are crucial for advancing solar energy conversion and storage technologies. In this study, we designed and synthesized a novel organic dye, denoted as YB6, for p‐type dye‐sensitized solar cells (p‐DSCs) and photoelectrochemical H2O2 production. YB6 features an extended conjugated π‐bridge derived from indacenodithieno[3,2‐b]thiophene and exhibits notable advantages: a two‐fold higher molar extinction coefficient at its main absorption peak and a broader absorption as compared to the PB6 dye. In p‐type dye‐sensitized NiO photoelectrochemical cells, the YB6‐based device demonstrated superior performance as compared to the PB6‐based device. It delivered nearly a 50 % higher H2O2 production over 5 hours. Furthermore, when fabricated into p‐DSCs, the YB6‐based device exhibited a 33 % higher power conversion efficiency. This enhancement is caused by suppressed charge recombination from the dye structure, which in turn may be traced to a larger thermodynamic up‐hill process for recombination losses in the YB6‐based system.

"Two-Stage Rocket-Propelled" Strategy Boosting Theranostic Efficacy with Mitochondria-Specific Type I-II Photosensitizers.

Imaging-guided photodynamic therapy (PDT) holds great potential for tumor therapy. However, achieving the synergistic enhancement of the reactive oxygen species (ROS) generation efficiency and fluorescence emission of photosensitizers (PSs) remains a challenge, resulting in suboptimal image guidance and theranostic efficacy. The hypoxic tumor microenvironment also hinders the efficacy of PDT. Herein, we propose a "two-stage rocket-propelled" photosensitive system for tumor cell ablation. This system utilizes MitoS, a mitochondria-targeted PS, to ablate tumor cells. Importantly, MitoS can react with HClO to generate a more efficient PS, MitoSO, with a significantly improved fluorescence quantum yield. Both MitoS and MitoSO exhibit less O2-dependent type I ROS generation capability, inducing apoptosis and ferroptosis. In vivo PDT results confirm that this mitochondrial-specific type I-II cascade phototherapeutic strategy is a potent intervention for tumor downstaging. This study not only sheds light on the correlation between the PS structure and the ROS generation pathway but also proposes a novel and effective strategy for tumor downstaging intervention.

Hydrophilic Biocompatible Fluorescent Organic Nanoparticles as Nanocarriers for Biosourced Photosensitizers for Photodynamic Therapy.

Most photosensitizers of interest for photodynamic therapy-especially porphyrinoids and chlorins-are hydrophobic. To circumvent this difficulty, the use of nanocarriers is an attractive strategy. In this perspective, we have developed highly water-soluble and biocompatible fluorescent organic nanoparticles (FONPs) made from citric acid and diethyltriamine which are then activated by ethlynene diamine as nanoplatforms for efficient photosensitizers (PSs). Purpurin 18 (Pp18) was selected as a biosourced chlorin photosensitizer combining the efficient single oxygen generation ability and suitable absorption in the biological spectral window. The simple reaction of activated FONPs with Pp18, which contains a reactive anhydride ring, yielded nanoparticles containing both Pp18 and Cp6 derivatives. These functionalized nanoparticles combine solubility in water, high singlet oxygen generation quantum yield in aqueous media (0.72) and absorption both in the near UV region (FONPS) and in the visible region (Soret band approximately 420 nm as well as Q bands at 500 nm, 560 nm, 660 nm and 710 nm). The functionalized nanoparticles retain the blue fluorescence of FONPs when excited in the near UV region but also show deep-red or NIR fluorescence when excited in the visible absorption bands of the PSs (typically at 520 nm, 660 nm or 710 nm). Moreover, these nanoparticles behave as efficient photosensitizers inducing colorectal cancer cell (HCT116 and HT-29 cell lines) death upon illumination at 650 nm. Half maximal inhibitory concentration (IC50) values down to, respectively, 0.04 and 0.13 nmol/mL were observed showing the potential of FONPs[Cp6] for the PDT treatment of cancer. In conclusion, we have shown that these novel biocompatible nanoparticles, which can be elaborated from biosourced components, both show deep-red emission upon excitation in the red region and are able to produce singlet oxygen with high efficiency in aqueous environments. Moreover, they show high PDT efficiency on colorectal cancer cells upon excitation in the deep red region. As such, these functional organic nanoparticles hold promise both for PDT treatment and theranostics.

LASU: An efficient and stable phthalocyanine dye with tolerable safety profile for self-disinfecting anti-COVID textiles activated by ambient light

BackgroundRecent COVID crisis has demonstrated that modern society urgently needs an accessible protection against mass infections, especially viruses, as the new strains are appearing at an ever-increasing pace and cause severe harm to the population and the world economy. MethodsWe have developed an efficient phthalocyanine photosensitizer LASU, that is suitable for dyeing textiles and allows to prepare reusable self-disinfecting fabrics with strong antiviral properties. The safety profile of LASU was evaluated in accredited laboratories by several in vitro assays according to the OECD-guidelines. ResultsThe textiles impregnated with LASU phthalocyanine showed a significant antiviral photodynamic effect even under moderate indoor and outdoor light. The dye did not show any genotoxic potential in human lymphocyte micronucleus assay. It showed a possible indication for eye irritation in human EpiOcular™ model and was phototoxic when tested in mouse BALB/c 3T3 cell test in the presence and absence of UVA-irradiation. ConclusionNovel phthalocyanine-dyed textiles are suitable for general use as self-disinfecting antiviral barriers and materials in hospitals, households, and public places. The safety profile of LASU is the phototoxic effect which is related to LASU´s mode of action.

Photodynamic inactivation of Listeria monocytogenes using a natural aggregation-induced emission photosensitizer and its application in salmon preservation

Photodynamic sterilization has been regarded as a promising alternative to conventional antibacterial approaches. However, the photodynamic efficiency of conventional photosensitizer is often compromised by aggregation-induced quenching effects. Photosensitizers, especially natural products, with aggregation-induced emission (AIE) properties open a new avenue for photodynamic sterilization. Herein, we investigated the photodynamic antibacterial performance and mechanism of the AIE-type natural product of berberine (BBR) against Listeria monocytogenes (L. monocytogenes). The bactericidal effect was assessed through the determination of minimum bactericidal concentration and implementation of anti-biofilm experiments. The results showed that BBR can significantly suppress the proliferation of L. monocytogenes and can efficiently remove the L. monocytogenes-derived biofilm in a concentration-dependent trend. The mechanism of killing L. monocytogenes has been speculated based on bacterial morphology characterization, viability staining results, enzyme activity assays, DNA electrophoresis analysis, and molecular docking. The excellent anti-bacterial activity of BBR mediated photodynamic process may account for its abilities to the irreversibly disruption of bacterial membrane, inhibition of intracellular enzyme activity and decomposition of intracellular DNA molecules. We also demonstrated that BBR embedded sodium alginate/chitosan packaging film is feasible to maintain the freshness of salmon under light illumination by inhibiting the bacterial proliferation.

Computational, experimental investigations on organic Solanum nigrum fruit extract sensitized titanium dioxide for enhanced photovoltaic performance

Natural dye decorated titanium dioxide nanoparticles were synthesized in a single step by modifying the conventional sol – gel method. The colored titanium dioxide (TiO2) was the outcome of the adding up the dye sensitizer during the synthesis itself. An efficient natural photo sensitizer was extracted from Solanum nigrum fruits which contains gallic acid and catechin as major pigments. The untainted TiO2 was blended via conventional sol – gel scheme and colored TiO2 nanoparticles synthesized via improved sol – gel and are sensitized by Solanum nigrum organic photo sensitizer. In order to study the structural, symmetrical, optical, spectral and morphological belongings were inspected by utilizing x- ray diffraction, transmission electron microscope, Fourier transform infra-red spectroscopy and UV – vis spectral analyses. The adsorption of colorant molecule on TiO2 exterior enhances the structural, vibrational mode symmetries deliberated. The optimized molecular structure of Gallic acid and Catechin were premeditated via Density functional theory. Their FMOs analyses and molecular electrostatic potential reactivity analysis were also premeditated. The efficiency studies reveal that the natural DSSCs made-up by utilizing colored TiO2 showed 63 % improvement in efficiency over the pure TiO2 based DSSC. This is credited to single step altered sol–gel practice which enhanced the morphology, dye adsorption and abridged the agglomeration, dye aggregation in TiO2 nanoparticles which has improved the efficiency.

Near IR light sensitization modulated to self-assembled CuO–CuxS nanorods thin films

An assembled CuO-CuxS nanorods heterostructure has been produced by liquid chemical conversion and wet etching of the Cu thin film. The chemical etching and anionic exchange modify and convert the Cu thin film to self-assembled CuO/CuxS random nanorods. The enhanced near infrared (NIR) light absorption capability and the effective separation of electron–hole pairs generated by the conjugated CuO-CuxS nanorods complement high visible (especially red) light driven photocatalytic activities as well as NIR photodetecting performances.The surface morphology, chemical content, crystalline analysis and structural vibrations of the CuO/CuxS nanorods were characterized using field emission scanning electron microscopy (FESEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD) and Raman scattering, respectively. Diffuse reflectance spectroscopy was utilized to evaluate optical properties of the CuO-CuxS nanorods. The assembled CuO–CuxS nanorods thin film exhibits good crystallinity with superior reproducibility and high selectivity for NIR absorption. The CuxS coupling into CuO is also responsible to surface enhanced Raman scattering. The static and high frequency dielectric constant, Urbach tail, optical carrier density and nonlinear refractive index have been estimated. The bandgap energy and optical carrier density are estimated around 1.22 eV and 1027 m−3, respectively. The photoharvesting performance was characterized using under sunlight illumination, and green, red and NIR laser irradiation. The CuO–CuxS hetero-interface manipulate charge transferring of the photoinduced carriers, which promotes the photodegradation efficiency of Methylene blue (MB) and NIR photosensitization.

Unexpected longer T1 lifetime of 6-sulfur guanine than 6-selenium guanine: the solvent effect of hydrogen bonds to brake the triplet decay.

The decay of the T1 state to the ground state is an essential property of photosensitizers because it decides the lifetime of excited states and, thus, the time window for sensitization. The sulfur/selenium substitution of carbonyl groups can red-shift absorption spectra and enhance the triplet yield because of the large spin-orbit coupling, modifying nucleobases to potential photosensitizers for various applications. However, replacing sulfur with selenium will also cause a much shorter T1 lifetime. Experimental studies found that the triplet decay rate of 6-seleno guanine (6SeGua) is 835 times faster than that of 6-thio guanine (6tGua) in aqueous solution. In this work, we reveal the mechanism of the T1 decay difference between 6SeGua and 6tGua by computing the activation energy and spin-orbit coupling for rate calculation. The solvent effect of water is treated with explicit microsolvation and implicit solvent models. We find that the hydrogen bond between the sulfur atom of 6tGua and the water molecule can brake the triplet decay, which is weaker in 6SeGua. This difference is crucial to explain the relatively long T1 lifetime of 6tGua in an aqueous solution. This insight emphasizes the role of solvents in modulating the excited state dynamics and the efficiency of photosensitizers, particularly in aqueous environments.

The photosensitizer system based on cationic COF carrier with the loading tetraminoporphyrin and its combined antibacterial effect

The 2D covalent organic framework COFTGTp was synthesized and TAPP deposited on it via π–π interactions to form TAPP/COFTGTp. Excellent antibacterial effect against both Gram-positive and Gram-negative bacteria was achieved with good biosafety.

Biodegradable fluorescent protein chromophore nanoparticles for hypoxic two-photon photodynamic therapy.

In this paper, biodegradable red fluorescent protein (RFP) chromophore analogue DPFP-SS-FA nanoparticles were synthesized for hypoxic two-photon photodynamic therapy. The maximum emission wavelength of DPFP-SS-FA is in the red-to-near-infrared region at 674 nm. Interestingly, these DPFP-SS-FA nanoparticles remain stable under physiological conditions, but deplete glutathione and disintegrate into the RFP chromophore analogue monomer in the tumor microenvironment. Meanwhile, electron paramagnetic resonance data have shown that DPFP-SS-FA produced enhanced 1O2/O2˙- signals after glutathione depletion causing an enhanced PDT effect. DPFP-SS-FA has negligible cell dark toxicity and high phototoxicity in hypoxic environments, indicating the outstanding hypoxia-overcoming ability of DPFP-SS-FA. In addition, due to its folic acid receptor and lysosome dual-targeting ability, DPFP-SS-FA is highly enriched in A-549 tumor cells. In particular, the hypoxic two-photon photodynamic therapy mediated by DPFP-SS-FA nanoparticles was validated in a zebrafish tumor model. Under 800 nm two-photon excitation, DPFP-SS-FA enabled bright two-photon fluorescence imaging and significantly inhibited the growth of tumor cells in zebrafish. The biodegradable DPFP-SS-FA nanoparticles reasonably constructed in this study can serve as excellent candidates for efficient hypoxic two-photon photosensitizers to treat deep tumor tissues.

Confined semiconducting polymers with boosted NIR light-triggered H2O2 production for hypoxia-tolerant persistent photodynamic therapy.

Hypoxia featured in malignant tumors and the short lifespan of photo-induced reactive oxygen species (ROS) are two major issues that limit the efficiency of photodynamic therapy (PDT) in oncotherapy. Developing efficient type-I photosensitizers with long-term ˙OH generation ability provides a possible solution. Herein, a semiconducting polymer-based photosensitizer PCPDTBT was found to generate 1O2, ˙OH, and H2O2 through type-I/II PDT paths. After encapsulation within a mesoporous silica matrix, the NIR-II fluorescence and ROS generation are enhanced by 3-4 times compared with the traditional phase transfer method, which can be attributed to the excited-state lifetime being prolonged by one order of magnitude, resulting from restricted nonradiative decay channels, as confirmed by femtosecond spectroscopy. Notably, H2O2 production reaches 15.8 μM min-1 under a 730 nm laser (80 mW cm-2). Further adsorption of Fe2+ ions on mesoporous silica not only improves the loading capacity of the chemotherapy drug doxorubicin but also triggers a Fenton reaction with photo-generated H2O2 in situ to produce ˙OH continuously after the termination of laser irradiation. Thus, semiconducting polymer-based nanocomposites enables NIR-II fluorescence imaging guided persistent PDT under hypoxic conditions. This work provides a promising paradigm to fabricate persistent photodynamic therapy platforms for hypoxia-tolerant phototheranostics.

Iridium(III) complexes decorated with silicane-modified rhodamine: near-infrared light-initiated photosensitizers for efficient deep-tissue penetration photodynamic therapy.

Meeting the demand for efficient photosensitizers in photodynamic therapy (PDT), a series of iridium(III) complexes decorated with silicane-modified rhodamine (Si-rhodamine) was meticulously designed and synthesized. These complexes demonstrate exceptional PDT potential owing to their strong absorption in the near-infrared (NIR) spectrum, particularly responsive to 808 nm laser stimulation. This feature is pivotal, enabling deep-penetration laser excitation and overcoming depth-related challenges in clinical PDT applications. The molecular structures of these complexes allow for reliable tuning of singlet oxygen generation with NIR excitation, through modification of the cyclometalating ligand. Notably, one of the complexes (4) exhibits a remarkable ROS quantum yield of 0.69. In vivo results underscore the efficacy of 4, showcasing significant tumor regression at depths of up to 8.4 mm. This study introduces a promising paradigm for designing photosensitizers capable of harnessing NIR light effectively for deep PDT applications.

Dual Solar-Driven Hydrogen Evolution and Alcohol Oxidation with CdS Quantum Dot-Sensitized Photocatalysis Prepared by SILAR Methodology

Quantum dots (QDs) have gained significant attention as efficient photosensitizers for light-harnessing applications. While quantum dots are extensively employed in dye-sensitized solar cells (DSSCs), their exploration as sensitizers on metal...

A fully conjugated imidazole-fused perylene phenantroline ruthenium(II) complex in photocatalytic oxidation

In this investigation, the suitability of a specially designed imidazole-fused perylene ruthenium(II) molecule, denoted as Ru-PhP, was explored by employing the photooxidation of 1,5-dihydroxynaphthalene (DHN) to produce Juglone as a model reaction. This distinctive, entirely conjugated compound was synthesized through the reaction between perylene imide anhydride dye (1) and a ruthenium(II) phenanthroline complex (2) in the presence of a Zn(OAc)2 catalyst. Structural analyses of the compound were performed by using general spectroscopic methods including FT-IR, 1H NMR, 13C- NMR, and MALDI-TOF analyses. Various photophysical properties, including the UV–Vis absorption spectrum, fluorescence emission spectrum, and fluorescence quantum yield, were examined. The photochemical studies via indirect method endorsed Ru-PhP as an efficient photosensitizer. Furthermore, Ru-PhP proved to be highly effective in facilitating the photooxidation of DHN to yield juglone. DFT-based natural bond orbital analysis revealed intramolecular charge transfer in Ru(II) coordination environment, with a strong total stabilization energy (25.31 eV) between the ruthenium acceptor and nitrogen donors in the bipyridine and phenanthroline units. The dispersion of HOMO electrons within the imidazole-bridged perylene moiety and the localization of LUMO electrons near Ru(II)-coordinated bipyridine units were observed through Frontier Molecular Orbital and molecular electrostatic potential analyses. Ru-PhP is proposed as photocatalyst for photo redox catalytic organic reactions.

Superoxide radical generator based on triphenylamine-based supramolecular organic framework for green light photocatalysis

Supramolecular organic frameworks (SOFs) mostly require high-energy purple or blue light for photocatalytic reactions, while highly abundant and low-energy light systems have rarely been explored. Therefore, it is necessary to construct 2D SOFs for low-energy light-induced photocatalysis. This study describes the design and synthesis of a water-soluble two-dimensional (2D) supramolecular organic framework (TP-SOF) using the host–guest interaction between a triphenylamine derivative (TP-3Py) and cucurbit[8]uril (CB[8]). The formation of the 2D SOF can be attributed to the synergistic impact resulting from the orientated head-to-tail superposition mode between the vinylpyridine arms of TP-3Py and CB[8], which results in a significant redshift in the UV–vis absorption spectrum, especially displaying a strong absorption band in the green light region. The monomeric TP-3Py can effectively produce singlet oxygen (1O2) and realize the photocatalytic oxidation of thioanisole in the aqueous solution. In comparison to monomeric TP-3Py, the confinement effect of CB[8] results in a notable enhancement in the production efficiency of superoxide anion radicals (O2•−), exhibiting promising prospects in the field of photocatalytic oxidation reaction, which facilitates the application of TP-SOF as a very efficient photosensitizer for the promotion of the oxidative hydroxylation of arylboronic acids under green light in the aqueous solution, giving a high yield of 91%. The present study not only presents a compelling illustration of photocatalysis utilizing a 2D SOF derived from triphenylamine, but also unveils promising avenues for the photocatalytic oxidation of SOF employing low-energy light systems.