Alkoxy Chains Research Articles

Silver Dendritic Gels with Luminescence and Aggregation-Induced Emission Effect.

This work reports on a novel family of silver metallogels based on discrete coordination complexes. Structurally, they consist of dendrimers containing a trinuclear silver metallacycle at the core, with the general formula [M(μ-pz)]3, and poly(benzyl)ether branched structures with different numbers or terminal alkoxy chains at the periphery. These silver metallodendrimers are able to gel low-polarity solvents such as dodecane or cyclohexane, giving rise to luminescent organogels at room temperature with the property of aggregation-induced emission (AIE). This property means that in solution or the sol state, they are weak emitters, but in the gel state, luminescence is considerably increased. In this particular case, they exhibit blue luminescence. Two different dendritic scaffolds have been studied, finding significant differences in solubility, gel formation and dependence of luminescence on temperature. The results show that properly tailored silver gelators can show luminescence in the gel state.

Tuning photovoltaic parameters in polymer solar cells through side-chain modification of donor polymer based on cyclopenta[c]thiophene-4,6(5H)-dione

Conjugated polymers were developed by using thiophene-dione derivatives named DEHOB-BDTF and DBOOB-BDTF. The polymers have a combination of electron donor (D) and electron acceptor (A), in which 5-(3,4-bis(((2-ethylhexyl)oxy)benzylidene)-1,3-dibromo-4H-cyclopenta[c]thiophene-4,6(5H)-dione (DEHOB) or 5-(3,4-bis((2-butyloctyl)oxy)benzylidene)-1,3-dibromo-4H-cyclopenta[c]thiophene-4,6(5H)-dione (DBOOB) serves as the electron acceptor units. The alkoxy chain shows strong electron-donating properties due to conjugation effects while longer alkoxy chain increases the solubility. Non-fullerene PSCs are fabricated with an ITO/ZnO/polymer: Y6BO/MoO3/Ag structure in which Y6BO is used as an electron acceptor. The performance of the device by using DEHOB-BDTF is accomplished up to 8.49 % (an open-circuit voltage of 0.85 V and a short-circuit current density of 20.1 mA/cm2). Furthermore, the longer alkoxy chain length enhances solubility making a well-ordering in DBOOB and reaching the fill factor of 54.2 %, due to the extended alkoxy chain can improve the miscibility in the blend.

Biphenyl based schiff base derivatives of 6-aminocoumarin: Design, synthesis, mesomorphic properties and DFT studies

The study focused on synthesizing two series of coumarin Schiff base liquid crystals. These series involved molecules with variations in alkoxy chains at aldehyde ends: one being the Schiff base with 4′‑hydroxy-[1,1′]-biphenyl-4-carbaldehyde (ASBP series) and the other being alkyl 4-formyl-[1,1′]-biphenyl-4-carboxylate (AEBP series). The compounds were characterized using FTIR, NMR, and Mass spectral analyses. All the compounds were studied for their mesomorphic properties, differential scanning calorimetry (DSC) and polarized optical microscopy (POM). In both the homologous series, variation of alkyl chain length showed intriguing phase transitions. In the first homologous series ASBP, compound with hexyloxy chain displayed an enantiotropic nematic (N) phase, while those with chain lengths n = 8–16 exhibited enantiotropic smectic A (SmA) mesophase. Similarly, in the AEBP series, compounds with n = 6,8 chain length showed an enantiotropic nematic (N) phase, while those with higher chain lengths n = 10–16 exhibited enantiotropic smectic A (SmA) phases. SmA mesophase was further confirmed by powdered XRD analysis. The study included DFT theoretical calculations to comprehend the compounds' mesomorphic behavior, comparing them with analogous reported compounds. Additionally, the investigation correlated experimental findings of individual compounds with calculated parameters like polarizability, dipole moment, and aspect ratio. Molecular electrostatic potential projections and analysis of frontier molecular orbitals were also employed to elucidate how polarity variations in terminal chains and mesogenic cores influenced the energy gap of FMOs and the distribution of electrostatic charges on these compounds. It has been found that the ASBP series has lower energy gap and higher dipole moment than the AEBP series.

Gold(III), Mercury(II), and Palladium(II) Complexes of a Series of Isomeric Bis(mono- and dialkoxyphenyl)pyridines: Introduction of Gold through Transmetalation and Catalysis.

A series of isomeric bis-2,6-(monoalkoxyphenyl)pyridine and bis-2,6-(dialkoxyphenyl)pyridine ligands were synthesized and characterized. In order to prepare their chlorogold(III) complexes, intermediate chloromercury(II) complexes were first prepared, but unlike observations from previous studies where they were obtained impure and at best in moderate yield, here pure complexes were synthesized, many in rather high yields. Depending on the substitution pattern of the alkoxy chains on the ligands, mono- and/or dimercurated complexes were obtained, characterized by 1H, 13C{1H}, and 199Hg NMR spectroscopy as well as, in several cases, by X-ray crystallography. Factors that may explain this unusual reactivity are discussed. In most cases, transmetalation to the related chlorogold(III) complex proceeded smoothly, although lower yields were obtained when starting from doubly mercurated precursors. Prompted by the propensity of these ligands to mercurate, attempts were made to effect direct auration, but none was successful. However, dimeric, orthometalated complexes of palladium(II) could be prepared and were also amenable to transmetalation to the chlorogold(III) complex, providing for a mercury-free synthesis.

Completely Non‐Fused Low‐Cost Acceptor Enables Organic Photovoltaic Cells with 17 % Efficiency

AbstractTo meet the industrial requirements of organic photovoltaic (OPV) cells, it is imperative to accelerate the development of cost‐effective materials. Thiophene‐benzene‐thiophene central unit‐based acceptors possess the advantage of low synthetic cost, while their power conversion efficiency (PCE) is relatively low. Here, by incorporating a para‐substituted benzene unit and 1st‐position branched alkoxy chains with large steric hindrance, a completely non‐fused non‐fullerene acceptor, TBT‐26, was designed and synthesized. The narrow band gap of 1.38 eV ensures the effective utilization of sunlight. The favorable phase separation morphology of TBT‐26‐based blend film facilitates the efficient exciton dissociation and charge transport in corresponding OPV cell. Therefore, the TBT‐26‐based small‐area cell achieves an impressive PCE of 17.0 %, which is the highest value of completely non‐fused OPV cells. Additionally, we successfully demonstrated the scalability of this design by fabricating a 28.8 cm2 module with a high PCE of 14.3 %. Overall, our work provides a practical molecular design strategy for developing high‐performance and low‐cost acceptors, paving the way for industrial applications of OPV technology.

Completely Non-Fused Low-Cost Acceptor Enables Organic Photovoltaic Cells with 17 % Efficiency.

To meet the industrial requirements of organic photovoltaic (OPV) cells, it is imperative to accelerate the development of cost-effective materials. Thiophene-benzene-thiophene central unit-based acceptors possess the advantage of low synthetic cost, while their power conversion efficiency (PCE) is relatively low. Here, by incorporating a para-substituted benzene unit and 1st-position branched alkoxy chains with large steric hindrance, a completely non-fused non-fullerene acceptor, TBT-26, was designed and synthesized. The narrow band gap of 1.38 eV ensures the effective utilization of sunlight. The favorable phase separation morphology of TBT-26-based blend film facilitates the efficient exciton dissociation and charge transport in corresponding OPV cell. Therefore, the TBT-26-based small-area cell achieves an impressive PCE of 17.0 %, which is the highest value of completely non-fused OPV cells. Additionally, we successfully demonstrated the scalability of this design by fabricating a 28.8 cm2 module with a high PCE of 14.3 %. Overall, our work provides a practical molecular design strategy for developing high-performance and low-cost acceptors, paving the way for industrial applications of OPV technology.

Multi-cation alkoxy chains with high ion conductivity and durability in cross-linked poly (aryl piperidinium) anion exchange membranes

AEMs with high ionic conductivity and excellent alkali stability are one of the cores to ensure that AEMWE achieves high performance. For the current problems of AEMs, multi-cation side chain crosslinkers present a mitigation strategy for the inherent “trade-off” between ion conductivity and mechanical strength and ensure exceptional alkali resistance. Herein, we introduced the first report on cross-linked AEMs with several hydrophilic multi-cation alkoxy chains, featuring ethylene oxide (EO). The differentiation in the hydrophilic/hydrophobic microphase separation structures, characterized by varying positions of the alkoxy chains within the three-stage multi-cation crosslinker, was explored by experiments and simulation, as well as bearing on the comprehensive performance of AEMs. Notably, EO located in the middle of multi-cations crosslinker was found to establish a coherent and ordered ion channel. QPTP-NOBN15 AEM exhibited the highest OH− conductivity (166.6 mS cm−1) and demonstrated lower water uptake (44.4 %) and swelling ratio (14.5 %) at 80°C. And meticulously designed cross-linked structures, along with ether-free backbones, bestowed upon QPTP-NOBN15 impressive alkali stability. After being retained in 1 M KOH solutions for 1200 h, ion conductivity of QPTP-NOBN15 remained largely unaffected. Furthermore, QPTP-NOBN15-MEA was evaluated by water electrolysis in 1 M KOH solutions at 60°C and found that the current density reached 1.8 A cm−2 at 2.99 V.

Cross-coupling and dehalogenation reactions of novel π-conjugated polymers bearing high-soluble coumarin unit in the main chain and their acid-base responsive fluorescence

A highly soluble coumarin monomer, 3,7-dibromo-4-octyloxycoumarin, was developed as the novel building block for π−conjugated polymers. Sonogashira coupling reaction, dehalogenation reaction, and Suzuki-Miyaura coupling reaction were carried out by using this new monomer as the main chain unit of π−conjugated polymer for polymerization. Introduction of a long alkoxy chain into coumarin monomer unit significantly improved the solubility of thus obtained polymers. The absorption and emission spectra of polymers showed red-shift compared to those of monomer, indicating the expansion of the π−conjugated system in the polymer main chain. Especially the polymers synthesized via Sonogashira coupling formed excimer in film state. The polymers showed acid-base responsibility with the addition of KOHaq and HClaq.

High Open-Circuit Voltage Organic Solar Cells with 19.2% Efficiency Enabled by Synergistic Side-Chain Engineering.

Restricted by the energy-gap law, state-of-the-art organic solar cells (OSCs) exhibit relatively low open-circuit voltage (VOC) because of large nonradiative energy losses (ΔEnonrad). Moreover, the trade-off between VOC and external quantum efficiency (EQE) of OSCs is more distinctive; the power conversion efficiencies (PCEs) of OSCs are still <15% with VOCs of >1.0V. Herein, the electronic properties and aggregation behaviors of non-fullerene acceptors (NFAs) are carefully considered and then a new NFA (Z19) is delicately designed by simultaneously introducing alkoxy and phenyl-substituted alkyl chains to the conjugated backbone. Z19 exhibits a hypochromatic-shifted absorption spectrum, high-lying lowest unoccupied molecular orbital energy level and ordered 2D packing mode. The D18:Z19-based blend film exhibits favorable phase separation with face-on dominated molecular orientation, facilitating charge transport properties. Consequently, D18:Z19 binary devices afford an exciting PCE of 19.2% with a high VOC of 1.002V, surpassing Y6-2O-based devices. The former is the highest PCE reported to date for OSCs with VOCs of >1.0V. Moreover, theΔEnonrad of Z19- (0.200eV) and Y6-2O-based (0.155eV) devices are lower than that of Y6-based (0.239eV) devices. Indications are that the design of such NFA, considering the energy-gap law, could promote a new breakthrough in OSCs.

Synthesis of Alkoxy-TEMPO Aminoxyl Radicals and Electrochemical Characterization in Acetonitrile for Energy Storage Applications

In this paper, we describe the synthesis and characterization of alkoxylated TEMPO, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl, radicals with potential application in organic non-aqueous redox flow batteries. The behavior of a series of TEMPO derivatives with varying lengths of alkoxy chain is analyzed in acetonitrile solutions using electrochemical techniques, electron paramagnetic resonance (EPR) spectroscopy, and measurements of permeability through three different membranes. Electrochemical redox potentials are only weakly dependent on the substituent, but, in contrast, exchange current densities derived from the data do depend on the substitution. EPR lends further insight into these properties via the determination of hyperfine splitting constant and rotational correlation time. There is a negligible effect of the substituents on those parameters among the modified TEMPO radicals. Finally, permeation rates of modified TEMPO derivatives through membranes depend significantly on both the membrane and the substitution of TEMPO, providing insights into capacity fade measurements in the literature.

Unsymmetrical and C3-Symmetrical Partially Fluorinated Hexaarylbenzenes: Effect of Terminal Alkoxy Chain Length on Photophysical and Thermophysical Behavior

Solution-state photoluminescence (PL) is affected by the electronic state; however, solid-state PL varies widely depending on the aggregated state. Although the synthesis and photophysical properties of unsymmetrical and C3-symmetrical hexaarylbenzenes (HABs) have been reported, the influence of their terminal alkoxy chains on their physical properties remains unclear. Therefore, we synthesized a series of unsymmetrical and C3-symmetrical partially fluorinated HABs with different alkoxy chains and investigated the effects of alkoxy chain length on the thermophysical and photophysical properties. While investigating phase transition behavior, the ethoxy-substituted unsymmetrical derivative revealed a columnar liquid-crystalline phase, whereas the other derivatives only exhibited a phase transition between crystalline and isotropic phases. While evaluating PL behavior, both the unsymmetrical and C3-symmetrical analogs exhibited relatively strong blue PL, independent of the alkoxy chain length. Through-space π-conjugation caused the PL spectra of C3-symmetrical derivatives to redshift compared to those of unsymmetrical derivatives. Partially fluorinated HABs exhibited relatively strong fluorescence, even in the crystalline state, depending on the alkoxy chain length, owing to the formation of various aggregated structures. Crystalline fluorinated HABs exhibited photochromism, resulting in the appearance of long-wavelength PL bands when exposed to ultraviolet (UV) irradiation, making them promising candidates for PL sensing materials for UV detection.

Synthesis, mesomorphic and magnetic properties at room temperature of biphenyl ester-aromatic imine with terminal alkoxy chains and methoxy substituent

ABSTRACT A series of calamitic biphenyl ester-aromatic imine derived from the reaction of 4-formylphenyl-4’-(alkyloxy)-[1,1’-biphenyl]-4-carboxylate and p-anisidine have been successfully synthesised and characterised. The general molecular structures of ultimate compounds show the central fragment made up by a hybrid core of biphenyl ester-aromatic imine in which the terminal alkoxy chains, CnH2n + 1 in which n = 7–12 were connected to biphenyl while the other end consists of methoxy moiety attached to a phenyl ring. All the target compounds under polarised lights exhibit enantiotropic nematic phase of which the temperature range was further supported by DSC analysis. It can be summarised that the lengthening of terminal alkoxy chains has contributed to the lowering of melting and clearing temperatures as well as the thermal stability of nematic phase. A dedicated magnetic characterisation analysis disclosed that apart from a dominant diamagnetic character these compounds possess a noticeable magnetic interaction despite knowing that the compounds belong to the non-metal and non-radical containing species.

Studies in synthesis of 6-aminocoumarin Schiff base derivatives as mesogens and their DFT approach

In first series, 6-amino coumarin Schiff base derivatives 10a-g were synthesized with alkoxy chain n = 6–18 and studied for their mesomorphic properties. In this series, compounds 10b with n = 8 showed monotropic nematic mesophase, while enantiotropic smectic A mesophase for higher analogues compounds 10c-g (with n = 10–18) was observed. In another series of Schiff base derivatives 12a-h additional ester linkage was introduced at the aldehyde end and were studied for their mesomorphic behavior. In second series, compounds 12a-c (with n = 4–8) showed enantiotropic nematic mesophase with very good thermal stability. Higher analogues of the second series with n = 12–18 showed stable enantiotropic smectic A mesophase. Compounds of both series were studied by DFT calculations. Different electronic parameters such as dipole moment, polarizability, molecular electrostatic potentials, frontier molecular orbitals, and thermodynamic variables were calculated and compared with the observed mesomorphic trends in both the studied series. Further, electronic parameters of compounds 10b and 12c and that of reference compound 4 were calculated and discussed to understand the effect of the removal of a hydroxyl group on the ortho position of the aldehyde part.

Novel liquid crystalline fluorene and fluorenone MIDA boronates: influence of alkyl vs alkoxy side chains on the mesomorphic properties

ABSTRACT To obtain novel boron liquid crystals, we successfully combined MIDA boronates with chromophoric fluorene and fluorenone mesogenic units and studied the influence of alkoxy versus alkyl side chains by differential scanning calorimetry (DSC), polarising optical microscopy (POM) and X-ray diffraction (XRD). The fluorenes showed broader temperature ranges of the SmA phase compared to their fluorenone counterparts. By replacing the alkoxy side chains with alkyl side chains, the mesophase ranges could be significantly enlarged and the thermal stability increased.

Aggregation-induced emission activity of sensor TBM-C1 hybrid of methoxy-triphenylamine (OMe-TPA) and dicyanovinyl for cyanide detection in aqueous THF: Mechanistic insights and potential applications

A series fluorescent probes (TBM-Cx (x = 1, 4, 8)) were designed based on embedding various alkoxy chains on the electron donor of triphenylamine (TPA)-based dicyanovinyl (MT) compound with an electron-deficient benzothiadiazole (BTD) for sensitive, selective, and visualizing detection of cyanide in aqueous solution. Due to the nucleophilic addition of CN−, the intramolecular charge transfer (ICT) of these probes was inhibited by the destroyed conjugated structure, exhibiting excellent “turn-on” fluorescence response toward cyanide anion (CN−) in tetrahydrofuran (THF). However, the alkoxy chains with different lengths embedded in TPA not only enhance the sensitivity and solubility, but also regulate the emission behavior from ICT to aggregation-induced emission (AIE) characteristics. The binding mechanism and AIE sensing performances between the probes and CN− have been investigated and compared in THF/water mixture by spectral tools and theoretical calculations. The results showed that the ICT-based TBM-C1 probe with methoxy chain showed significantly turn-on fluorescence response to CN− as low as 0.077 μM in THF/water solution at high water fraction (90 %). Due to the AIE sensing process, TBM-C1 was successfully employed to determine CN− in food and water samples, image CN− in living cells and BALB/c mice, and prepare test kits for visualizing cyanide.

Highly conductive alkoxy chain cross-linked poly (aryl piperidinium) anion exchange membrane for water electrolysis

Cross-linking represents a trenchant approach to coordinating the “trade-off” effect between ion conductivity and dimensional stability. Still, it is limited by the brittleness of materials caused by hydrophobic crosslinkers. We hereby introduced a hydrophilic alkoxy chain crosslinker containing dipolar molecules. The highly flexible C-O-C chain in the crosslinker allows for the formation of the hydrogen bond network, which amplifies the cation self-aggregation ability through Cation-Dipole interaction and constructs rational hydrophilic/hydrophobic microphase separation structures to establish a long-range ordered OH– pathway. Meanwhile, flexible crosslinkers suppressed swelling and enhanced flexibility. Among the alkoxy chain cross-linked poly (p-terphenyl piperidinium), QPTP-IEO15 exhibited the optimal OH– conductivity of 148.5 mS cm−1 at 80℃. Moreover, the QPTP-IEO15 membrane demonstrated remarkable alkaline stability while maintaining a low swelling ratio (15.0 % at 80℃) and adequate mechanical strength: ion conductivity and ion exchange capacity only deteriorated by 3.3 % and 2.9 % after soaking in a 1 M KOH solution (80℃) for 1200 h, respectively. Additionally, Anion exchange membrane water electrolysis based on QPTP-IEO15-MEA achieved a current density of 1800 mA cm−2 at 3.11 V.

CH3O Substitution Effect Revisited in the Vibrationally Resolved Laser-Induced Fluorescence Spectra of Methoxycyclohexoxy Radicals.

The oxy-substituted alkoxy radicals have attracted wide attention due to the increasing application of oxygenated volatile organic compounds as fuel additives and solvents. Direct detection of these intermediate radicals is desired for measuring the reaction rate and investigating the oxidation mechanism of organic compounds in the atmosphere. A charge-transfer excited state induced by CH3O substitution was identified in our previous study of 3-methoxy-1-propoxy radical [Xue, J. Phys. Chem. Chem. Phys. 2021, 23, 2586]. As the C-C bonds of chain alkoxy radicals can freely rotate, further studies are needed to understand the mechanism of this long-range charge-transfer effect. In this work, vibrational-resolved laser-induced fluorescence (LIF) spectra of 3- and 4-methoxycyclohexoxy radicals were obtained under jet-cooled conditions. A large red-shift of ∼454 cm-1 of the origin band was observed when the CH3O substituent moved from the δ site to the γ site of the cyclohexoxy radical. The LIF spectra are assigned to 3-cis (e, e) and 4-trans (e, e) conformers, respectively, with the assistance of structural optimization and electron excitation studies conducted at the CAM-B3LYP/6-311++G(d,p) level of theory. Natural transition orbital analysis reveals that the intramolecular charge transfer from the C-O-C p orbital to the radical O p orbital in 3-methoxycyclohexoxy has a strong effect on the radical CO σ → O p excitation and hence results in a spectral change. On the other hand, the spectral effect of CH3O substitution almost vanishes at δ carbon. The results propose a through-bond interaction between CH3O and radical CO groups.

Organic molecules with dual triplet‐harvesting channels enable efficient X‐ray scintillation and imaging

AbstractOrganic scintillators have recently gained considerable attentions in X‐ray detection for their potential applications in biomedical radiograph and security inspection. However, the weak X‐ray absorption and/or inefficient exciton utilization have limited the development and commercialization of organic scintillators. Currently, high‐performance X‐ray organic scintillators are scarce and organic scintillators with dual triplet‐harvesting channels have not been explored before. Here, we develop several proof‐of‐concept sulfone‐based organic molecules, C1–C7, using different alkoxy chains to manipulate molecular packing mode. These materials exhibit dual triplet‐harvesting channels of thermally activated delayed fluorescence (TADF) and room‐temperature phosphorescence (RTP) in aggregated state. Inspiringly, these molecules display distinct radioluminescence under the X‐ray stimulation. Among them, C6 behaves the highest light yield of 16,558 photons MeV−1. Moreover, clear X‐ray images are demonstrated in both aggregated state and single‐molecule level. High spatial resolutions of 15.0 and 10.6 line pairs per millimeter (lp mm−1) are achieved for rigid and flexible scintillator screens, exceeding most reported organic and conventional inorganic scintillators. These results highlight the great potential of organic molecules with TADF and RTP nature for efficient X‐ray scintillation and imaging.

Simple One–Pot Synthesis of Hexakis(2-alkoxy-1,5-phenyleneimine) Macrocycles by Precipitation–Driven Cyclization

Hexakis(2-alkoxy-1,5-phenyleneimine) macrocycles were synthesized using a simple one-pot procedure through precipitation-driven cyclization. The acetal-protected AB–type monomers, 2-alkoxy-5-aminobenzaldehyde diethyl acetals, underwent polycondensation in water or acid-containing tetrahydrofuran. The precipitation–driven cyclization, based on imine dynamic covalent chemistry and π–stacked columnar aggregation, played a decisive role in the one–pot synthesis. The progress of the reaction was analyzed using MALDI–TOF mass spectrometry. The macrocycles with alkoxy chains were soluble in specific organic solvents, such as chloroform, allowing their structures to be analyzed using NMR. The shape-anisotropic, nearly planar, and shape-persistent macrocycles aggregated into columnar assemblies in polymerization solvents, driven by aromatic π-stacking. The octyloxylated macrocycle OcO–Cm6 exhibited an enantiotropic columnar liquid crystal-like mesophase between 165 °C and 197 °C. In the SEM image of (S)-(–)-3,7-dimethyloctyloxylated macrocycle (–)BCO–Cm6, columnar substances with a diameter of 200–300 nm were observed. The polymerization solution for the 2-(2-methoxyethoxy)ethoxy)ethoxylated macrocycle (TEGO–Cm6) gelled, and showed thixotropic properties by forming a hydrogen bond network.

Water-soluble red fluorescent protein dimers for hypoxic two-photon photodynamic therapy.

In this study, two water-soluble red fluorescent protein (RFP) dimers, FP2R' and FP2R'', were synthesized by linking two phenothiazine-based RFP chromophore analogues through alkyl chains or alkoxy chains for hypoxic two-photon photodynamic therapy. RFP dimers are heavy-atom-free two-photon photosensitizers in which the intersystem crossing process is boosted by S and N heteroatoms. In terms of the aqueous solubility, the saturation concentration of FP2R'' was 3.5 mM, the emission wavelength was 677 nm, the singlet oxygen yield was 18%, and the two-photon absorption coefficient (β) was 2.1 × 10-11 cm W-1. Further, the RFP dimer FP2R'' showed excellent biocompatibility, negligible dark toxicity, and could produce 1O2 and O2˙- simultaneously. Under 460 nm illumination, the photosensitizer FP2R'' showed high phototoxicity with an IC50 value of 4.08 μM in an hypoxia environment, indicating that the photosensitizer FP2R'' has an excellent anti-hypoxia ability. In addition, the photosensitizer FP2R'' demonstrated a precise localization ability to lysosomes and its Pearson's colocalization coefficient was 0.94, which could guide the aggregation of photosensitizers in the lysosomes of tumor cells to effectively improve its photodynamic therapy (PDT) effect. In particular, when exposed to 800 nm two-photon excitation, FP2R'' effectively produced 1O2 and O2˙- in zebrafish and exhibited a bright two-photon fluorescence imaging capability. At the same time, the efficacy of two-photon photodynamic therapy mediated by the photosensitizer FP2R'' was verified in the tumor zebrafish model, and the growth of tumor cells in zebrafish was significantly inhibited under a two-photon laser irradiation. The water-soluble two-photon photosensitizer FP2R'' that was reasonably constructed in this study can be used as a high-efficiency hypoxic two-photon photosensitizer to inhibit deep tumor tissues.