Fully functionalizable triphenylamine with mono/di/tri α-aminophosphonates: synthesis, photophysical, morphological, and anticancer properties

IF 5.2 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-09-29 DOI:10.1016/j.molliq.2025.128625

A.S. Vijai Anand , S. Perinbanathan , A.S. Gokul , E. Veerashekhar Goud , Prabodh Ranjan , Rajagopal Desikan , C.V.S. Brahmananda Rao , Akella Sivaramakrishna

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引用次数: 0

Abstract

Organophosphonates are biogenic and xenobiotic compounds extensively utilized in a range of technological applications associated with agricultural, chemical, and pharmaceutical industries. In this regard, three novel mono/di/tri α-aminophosphonate-functionalized triphenylamines (mono- = CPMP, di- = CPDP, and tri- = CPTP) were synthesized through the formation of CP bonds. All the products were structurally characterized by spectroscopic and analytical techniques, including the single-crystal XRD analysis of CPMP. Furthermore, these newly identified probes showed remarkable photophysical properties in an array of organic solvents with high quantum yields. A unique and extremely high range of Stokes shifts (179–194 nm) was observed for these molecules. A notable aggregation behavior for CPMP, CPDP, and CPTP in the binary mixture (H₂O: THF, v/v) was observed through atomic force microscopic and scanning electron microscopic techniques by analyzing the particle topography and size of aggregated species. The data revealed that CPMP (70 % H₂O/THF), CPDP (70 % H₂O/THF), and CPTP (30 % H₂O/THF) exhibited significant emission levels. Additionally, the fluorophores were evaluated for MCF-7 (breast cancer cells), revealing an efficacy of IC₅₀ (37–49 μM) in inhibiting the growth of these cancer cells. The experimental validation was substantiated by the implementation of DFT calculations.

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具有单/二/三α-氨基膦酸盐的全功能化三苯胺：合成、光物理、形态和抗癌特性

有机膦酸盐是一种广泛应用于农业、化工和制药行业的生物源和外源化合物。为此，通过形成CP键合成了三种新型的单/二/三α-氨基膦酸功能化三苯胺（mono- = CPMP, di- = CPDP和tri- = CPTP）。通过光谱和分析技术，包括CPMP的单晶XRD分析，对产物进行了结构表征。此外，这些新鉴定的探针在一系列有机溶剂中表现出显著的光物理性质，具有高量子产率。观察到这些分子具有独特且极高的斯托克斯位移范围（179-194 nm）。通过原子力显微镜和扫描电镜技术分析了CPMP、CPDP和CPTP在二元混合物（H2O: THF, v/v）中的颗粒形貌和聚集物的大小，观察到CPMP、CPDP和CPTP有明显的聚集行为。CPMP （70% H2O/THF）、CPDP （70% H2O/THF）和CPTP （30% H2O/THF）表现出显著的排放水平。此外，对MCF-7（乳腺癌细胞）的荧光团进行了评估，揭示了IC50 （37-49 μM）对这些癌细胞生长的抑制作用。DFT计算的实现证实了实验的有效性。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.