NEW JOURNAL OF CHEMISTRY
·
2015
·Vol. 39
·期 7
·5750-5758
·
IF 3.086
Yinghui Bian,Jinshe Chen,Shaotang Xu,Yulu Zhou,Lijun Zhu,Yuzhi Xiang,Daohong Xia
Two novel metal-free phthalocyanines have been designed and synthesized, namely tetra{[1H-benzo(d)imidazol-2-yl]thiol}phthalocyanine (TBIT-Pc) and tetra{[benzo(d)thiazol-2-yl]thiol}phthalocyanine (TBTT-Pc). These two compounds showed similar structures, while imidazolyl-NH in the substitutes of TBIT-Pc could form more hydrogen bonds. TBIT-Pc and TBTT-Pc were fully characterized by elemental analysis, 1H NMR, MALDI-TOF MS, FT-IR and the UV-Vis absorption spectrum. The self-assembly properties of TBIT-Pc and TBTT-Pc were comparatively studied. TBIT-Pc and TBTT-Pc were present as monomers in DMF in the concentration range of 9.04–20.3 μM. Depending mainly on the intermolecular hydrogen bonding (N–H⋯N) between benzimidazole substitutes, “head-to-tail” J-aggregates of TBIT-Pc were formed in DMSO, while there was no aggregation of TBTT-Pc in the same solvent. “Face-to-face” H-aggregates of TBIT-Pc and TBTT-Pc were formed with the addition of water to the solutions of DMSO, and the degree of aggregation increased with the introduction of H-bonds (N–H⋯N) in the benzimidazole substitutes of TBIT-Pc. The atomic force microscope (AFM) image and dynamic light scattering (DLS) displayed the formation of well-defined nanoparticles with a diameter of ca. 30 ± 15 nm with J-type aggregation of TBIT-Pc. And the dendritic nanostructures with H-aggregates of TBIT-Pc and TBTT-Pc with different size were observed from transmission electron microscopy (TEM) images. The possible mechanism of the effect of H-bonds on the formation of J-aggregates of TBIT-Pc and the H-aggregation of TBIT-Pc and TBTT-Pc was also discussed. In the formation process of aggregates, H-bonds and π–π interaction may be the dominant factors. In addition, the nanostructures fabricated from TBIT-Pc and TBTT-Pc showed good semiconducting properties revealed by current–voltage measurements.
研究领域:
超分子化学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF COLLOID AND INTERFACE SCIENCE
·
2021
·
IF 8.128
Huiping Dang,Youliang Tian,Quan Cheng,Changchang Teng,Kai Xie,Lifeng Yan
It is essential to develop novel multifunctional and easily synthesized stable NIR-II fluorescent probes to guide photothermal therapy for tumors. Here, we propose a new strategy to construct boron dipyrromethene (BODIPY) J-aggregates by intermolecular hydrogen bonding (H-bond) and π-π stacking interactions to achieve fluorescence emission in the second near-infrared window (NIR-II, 1000–1700 nm). A novel meso -benzamide galactose hexanoate-BODIPY (Gal-OH-BDP) amphiphilic small molecular dye was synthesized and it formed nanoparticles spontaneously in aqueous solution with a maximum emission wavelength near 1060 nm, which works as a smart nanomedicine for targeting NIR-II imaging-guided photothermal therapy (PTT) of hepatocellular carcinoma. Galactose not only provided hydrogen bonds to regulate the aggregation pattern of the molecules but also effectively targeted hepatocellular carcinoma cells and promoted the formation of well-dispersed nanoparticles of dye molecules due to their hydrophilicity . Moreover, due to high photothermal conversion efficiency (PCE = 55%), Gal-OH-BDP NPs achieve galactose-targeted NIR-II imaging and PTT, which is important for the precise diagnosis and treatment of tumors ( Scheme 1 ). In the present research work, H-bond was introduced for the first time into BODIPY for building J-aggregates to achieve the NIR-II fluorescence.
研究领域:
生物医学工程
·
肿瘤学
·
纳米医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Advanced Healthcare Materials
·
2022
·Vol. 11
·期 15
·2200467
·
IF 11.092
Wansu Zhang,Shangyu Chen,Pengfei Sun,Shuai Ye,Quli Fan,Jun Song,Pengju Zeng,Junle Qu,Wai-Yeung Wong
The luminescence of traditional phosphorescence-based hypoxia probes is limited to the visible and first near-infrared wavelength regions (<1000 nm), which has defects of higher light scattering and lower penetration depth in contrast with the second near-infrared wavelength window (NIR-II, 1000–1700 nm) for optical bioimaging. Herein, 5,15-bis(2,6-bis(dodecyloxy)phenyl)-porphyrin platinum(II) (PpyPt) with J-aggregation induced NIR-II phosphorescence is reported. J-aggregates of PpyPt are confirmed by the X-ray diffraction data in the crystalline state. Moreover, the emission and excitation spectra of PpyPt in the solid states reveal NIR-II luminescence feature of PpyPt in J-aggregates. More importantly, by preparation of water-soluble PpyPt nanoparticles (PpyPt NPs 4.76 ) with J-aggregates, it has NIR-II phosphorescent lifetime of microseconds and good oxygen-sensitivity in water. Moreover, the good biological hypoxia-sensing potential of PpyPt NPs 4.76 is demonstrated in cells and 4T1-tumor-bearing mice. This study provides an efficient strategy to design NIR-II phosphorescent probe for sensitive tumor-hypoxia detection through the construction of J-aggregates.
研究领域:
生物医学工程
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光学成像
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材料科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
·
2019
·
IF 3.131
Kai Ma,Ran Wang,Tifeng Jiao,Jingxin Zhou,Lexin Zhang,Jinghong Li,Zhenhua Bai,Qiuming Peng
Constructing graphene oxide (GO)-based 2D nanomaterials via facile and appropriate methods have aroused much attention due to their potential applications in many fields. Herein, by Langmuir-Blodgett (LB) technique, we have successfully fabricated GO-based films composited with porphyrin molecules. By the reaction of diazotization and Fischer osazone, different surface states of GO sheets with sulfonate groups were obtained. The amphiphilic GO and surface modified GO sheets could spontaneously form composite films at the air/water interface with porphyrin molecules (TMPyP) by electrostatic interactions and π-π stacking. Since the sheets can perfectly float on the interface, the TMPyP molecules were adsorbed on the floating-layers and self-assembled into highly ordered J-aggregate structures. The morphological characterization results showed the composite films with smooth and dense surface. Due to the different surface state of the nanosheets, the aggregate states of porphyrin molecules were different which could be demonstrated in the UV–vis spectra. The results indicated that the induction of sulfonate groups and the types of oxygen-containing groups have played important roles for regulating the aggregate state of porphyrin molecules.
研究领域:
材料科学
·
化学
✓ 已验证
产品关联
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2025
·
IF 13.2
Taihe Han,Shuai Mu,Qin Huang,Jiaxing Sun,Xin Lv,Yanxia Zhang,Xiaoyan Liu,Wei Guo,Haixia Zhang
The development of high fluorescence quantum yield molecular fluorophores for second-order near-infrared (NIR-II) imaging is highly desirable but remains challenging due to the lack of reliable design guidelines. We report a method to construct “J-aggregates” by combining the inhibition of twisted intramolecular charge transfer (TICT) and electron-withdrawing strategies. Introducing electron-withdrawing substituents at the middle position of the classic boron dipyrromethene (BODIPY) backbone promotes J-type slip stacking, enhancing NIR-II fluorescence through increased electrostatic repulsion and intermolecular hydrogen bonding. The 3,5-aryl position is modified with sulfone and quaternary piperazine groups. The negative inductive effect (–I effect) from strong electron-withdrawing action increases the ionization potential (IP) of the amino group, inhibiting the TICT process and improving the quantum yield to 9.03 % and 16.9 %, respectively. Notably, the fluorescence quantum yield of NBDP-SO 2 increased to 18.2 % after self-assembly with F127, successfully applied in bioimaging. This study provides a new method for constructing high fluorescence quantum yield NIR-II emission by manipulating molecular stacking and establishing the relationship between molecular structure, intermolecular interactions, and fluorescence properties.
研究领域:
生物医学工程
·
分子影像学
✓ 已验证
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2024
·
IF 13.3
Fengxiang Tang,Haodong Yu,Yanzong Huang,Xue Zhao,Zixuan Chen,Honglin Ma,Bi-Yuan Zheng,Mei-Rong Ke,Yongfan Zhang,Xingshu Li,Juyoung Yoon,Jian-Dong Huang
Phthalocyanines (Pcs) are considered promising in cancer phototherapy. However, their maximum absorption wavelengths are only around 700 nm, which cannot allow deep tissue penetration and leads to poor therapeutic efficacy. To expand their clinical application, significantly shifting their absorption to longer wavelengths is urgently required. Dye J-aggregates exhibit a redshifted absorption relative to its monomer. However, Pc J-aggregates with enormous-redshifted and intense absorption is rarely reported, and little is known about the relationships between Pc structure and J-aggregation. Herein, such Pc J-aggregates are ingeniously conceived. With a yeast β -D-glucan-ursodeoxycholic acid conjugate as a potential tumor-associated macrophages (TAMs)-targeting carrier and 1-(4-carboxyethylphenoxy) zinc (II) phthalocyanine (Pc1) as a model, Pc1 J-aggregate nanoparticle (NanoPc1) is obtained via ultrasonication-aided emulsification-solvent evaporation technique. NanoPc1 displays strong absorption at 830 nm, with a 156 nm redshift. Further investigation on another twenty-four Pcs demonstrates that unsubstituted zinc (II) or magnesium (II) Pc and hydrophobic mono-substituted zinc (II) or magnesium (II) Pcs with mono-substituted phenoxy or phenylthio or naphthoxy as a substituent can readily form desired Pc J-aggregates with significant redshifts (140–165 nm). The other Pcs fail to form expected J-aggregates probably due to absence of central metals, steric hindrance on central metals (atoms), forming axial coordination on central metals, disorder tendency during self-assembly or hydrophilicity. The theoretical calculation indicates that Pc1 in its J-aggregates exhibits a spiral-like arrangement, and the reduction in the energy gap between HOMO and LUMO and variation of intermolecular π-π interaction caused by J-aggregate formation are responsible for the huge redshift. Additionally, using NanoPc1 as an exemplar, such Pc J-aggregate nanoparticles are substantiated to afford TAMs-targeted and efficient tri-modal imaging and photothermal therapy in a H22 mouse model.
研究领域:
生物医学工程
·
癌症治疗
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材料科学
·
分子生物学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF NANOBIOTECHNOLOGY
·
2025
·
IF 12.6
Kaiming He,Desheng Chen,Dongzi Zhu,Wenjie Zheng,Lei Lyu,Mingshen Zhang,Zeping Chen,Xiaowen Wang,Yongwei Hu,Binsheng Fu
Hepatocellular carcinoma (HCC) poses a significant therapeutic challenge, driving the need for novel treatment strategies. This study investigates the combination of photothermal therapy (PTT) and metalloimmunotherapy for HCC treatment using Co + diABZI@J-dICG nanoparticles. Indocyanine green (ICG), an FDA-approved near-infrared (NIR) dye, is dimerized into J-aggregates to enhance PTT by improving light absorption and photothermal efficiency. The cGAS-STING pathway, a key mediator of innate immunity, is activated by the STING agonist diABZI, while cobalt ions (Co 2+ ) further enhance immune responses. The Co + diABZI@J-dICG nanoparticles take advantage of ICG’s hepatotropic properties for sustained tumor accumulation and immune activation, resulting in significant tumor growth inhibition and reduced HCC recurrence following hepatectomy.
研究领域:
肿瘤学
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免疫学
·
纳米医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
iScience
·
2022
·
IF 6.107
Juexin Huang,Chuanliang Feng
Because any perturbation in the number of oxidation sites associated with the polymeric backbone can cause changes in the electrical properties, the stability of electrical properties has strongly prevented the wide adoption of most conducting polymers for commercialization, e.g., polyanilines (PANI). Herein, we showed that aniline dimers (AD) had more stable conductivity during redox due to their determinately separate oxidization or reduction units. Instead of intramolecular charge transfer as PANI, AD could serve as effective transfer units to facilitate intermolecular charge-carrier transmission due to low band-gap formation induced by the J-aggregation of AD, ensuring efficient conductivity. Typically, the electrical properties of AD-derived materials will still be stable after 10,000 redox cycles under a high operating voltage, far surpassing PANI under equivalent conditions. Meanwhile, the AD-derived materials could act as effective conducting and sensing layers with good stability. This approach opened an avenue for improving the stability of conductive polymers.
研究领域:
材料科学
·
化学
✓ 已验证
DOI
PubMed
高影响因子
ChemistrySelect
·
2022
·Vol. 7
·期 44
·e202203402
·
IF 2.307
Xiaoying Ma,Lei Shi,Yao Fu,Buyue Zhang,Xiufeng Zhang
Graphical The cyclic induction of H-aggregates and J-aggregates can be achieved by adding rare earth ions, methanol and EDTA to the MTC solution. The intuitive color expression can be used as a La 3+ detection switch. In recent years, the assembly of cyanine dye supramolecular aggregates has been a very important task because its photophysical and photochemical properties are widely used in many scientific fields, such as, materials, biomedical and industrial. In this work, H- and J-aggregates of cyanine dyes were constructed under controllable conditions, and a simple method was developed to achieve cycle induction around these aggregates which induced by rare earth ions, and the process can be repeated for many cycles. Assembly and circulation induce these aggregates to be easy to manipulate and identify, which can be directly observed with the naked eye. This simple supramolecular assembly provides another direction in the field of sensors, while bringing a new idea to the control of supramolecular aggregates.
研究领域:
材料科学
·
生物医学
·
工业化学
✓ 已验证
产品关联
DOI
高影响因子
CARBON
·
2023
·
IF 10.9
Cheng-Long Shen,Qing Lou,Kai-Kai Liu,Guang-Song Zheng,Run-Wei Song,Jin-Hao Zang,Lin Dong,Chong-Xin Shan
Control of aggregation plays an important role in the photophysical behavior of luminescent nanomaterials . Herein, the concentration-dependent self-assembled hybrid of carbon nanodots (CDs) with the alteration spectral characters of H-/J-aggregation were observed. In detail, the CDs aging under different conditions presented obvious spectral variations ranging from visible to near-infrared regions, accompanied by the spontaneous evolution of nanoaggregates from CD nanoparticles . Theoretical calculations and experimental results confirmed the inhomogeneous surface functional groups could render CDs into nanoaggregates with the H- or J-aggregation through intraparticle or interparticle interaction, inducing the discrepant surface-confined charges in these intraparticle nanoaggregates and further contributing to their shift of absorption and emission bands. With the novel aggregation regulation, the CDs exhibited a tunable increase in their photothermal and photodynamic capability in comparison to their original counterparts. These findings shed a new light on the understanding of the photophysical behaviors for the self-assembled hybrid of CDs with the concept of supramolecular engineering.
研究领域:
纳米材料科学
·
超分子工程学
✓ 已验证
产品关联
DOI
高影响因子
Materials Today Bio
·
2025
·
IF 10.2
Jiaqi Zhou,Hao Li,Hui Li,Jiayi Ding,Zhong Du,Jiabao Xiong,Hongyang Yao,Xueliang Zhang,Nuernisha Alifu,Biao Dong
Cyanine molecules with the second near-infrared (NIR-II) emission hold great potential for bioimaging owing to their great biocompatibility, but the scissor-like structure of these molecules poses a major bottleneck in obtaining efficient NIR-II fluorescence probes. Constructing J-aggregates represents a promising strategy for obtaining biomedical NIR-II emissive materials. However, achieving J-aggregates in cyanine dyes with large torsion angles between the heterocyclic rings poses a challenge. In this study, we introduced the guanidine of tumor molecular targeted peptide 1 (TMTP1) to increase steric hindrance of IR-783 and reduce the angle of IR-783 scissors. The near-coplanar structure of IR-783@peptide TMTP1 composite facilitates the formation of a novel J-aggregates (IR-783-LP-TMTP1) with super-stable effect for NIR-II in vivo dynamic vascular imaging and remarkable tumor targeting capbility. The stable emision wavelength and high spatial resolution of J-aggregates was demostrated for brain and ear vasculature bioimaging under 808 nm laser excitation. Additionally, J-aggregates exhibits robust tumor-targeting capability towards cervical tumors, indicating their potential in cervical cancer diagnosis. This work develops a molecular design strategy to construct bright NIR-II J-aggregates with super-stable and robust tumor-targeting properties and paving the way for improving bioimaging performance of similar molecules.
研究领域:
生物医学工程
·
分子影像学
·
纳米医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
·
2017
·
IF 2.714
Jingwen Song,Kai Ma,Tifeng Jiao,Ruirui Xing,Lexin Zhang,Jingxin Zhou,Qiuming Peng
Graphene oxide (GO)-based nanocomposite films via facile and appropriate self-assembly methods have demonstrated many potential applications in wide fields. This study demonstrates a facile and clean route to prepare graphene oxide-dye composite films using Langmuir-Blodgett (LB) technique at room temperature. By electrostatic interaction between cationic dye molecules and negatively charged GO sheets as well as π-π interactions, GO-dye composite LB films were formed spontaneously. As a soft platform for dye molecules, GO sheets induce dye molecules to self-assemble and form highly ordered structures containing H-aggregates and/or J-aggregates. The morphological characterization results show the formation of GO-dye composite films with smooth and dense surfaces. And the spectral results reveal that dye molecules stack in well-organized aggregates on the surface of GO sheets corresponding to monomers in bulk solution. The present research work about GO-dye composite films by LB method may provide new clues to prepare organized composite films and demonstrate potential applications in many fields.
研究领域:
材料科学
·
纳米科技
·
表面化学
·
胶体与界面科学
·
功能薄膜
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）