Synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations and characterization of 1,3-propanediylbis(triphenylphosphonium) monotribromide as brominating agent of double bonds and phenolic rings

Nokhbeh, Seyed Reza; Gholizadeh, Mostafa; Salimi, Alireza; Sparkes, Hazel A.

doi:10.1016/j.molstruc.2020.127700

Cited by 6 publications

(5 citation statements)

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“…This could be ascribed to the balance of the following two factors: on the one hand, the surface conjugation of cationic TPP partially neutralized the negative surface charge of GNPs and thus resulted in aggregation. On the other hand, the three noncoplanar benzene rings in the H 2 N-TPP molecules 25 provided enough steric hindrance for preventing the GNPs to form large aggregates. The TEM images of the GNA before and after coating with the CCM are shown in Figure 1A and 1B.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Portfolio Targeting Strategy To Realize the Assembly and Membrane Fusion-Mediated Delivery of Gold Nanoparticles to Mitochondria for Enhanced NIR Photothermal Therapies

et al. 2020

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Targeting mitochondria has always been a challenging goal for therapeutic nanoparticle agents due to their heterotypic features and size, which usually lead to a lysosome/endosome endocytosis pathway. To overcome this limitation, in this work, a portfolio targeting strategy combining a small targeting molecule with a biomembrane was developed. Modification of small targeting molecule H 2 N-TPP on gold nanoparticles (GNPs) could not only facilitate the mitochondrial targeting but could also induce gold nanoparticle assembly. Therefore, the GNPs were endowed with good absorption and photothermal conversion abilities in the near-infrared (NIR) region. Meanwhile, a biomimetic strategy was adopted by wrapping the gold nanoparticle assembly (GNA) with cancer cell membranes (CCMs), which helped the GNA enter the prostatic cancer cell via a homotypic membranefusion process to avoid being trapped in endosomes/lysosomes. Thereafter, the GNA remaining in the cytoplasm could reach mitochondria more efficiently via guidance from H 2 N-TPP molecules. This "biomembrane−small molecule" combination targeting process was evidenced by fluorescence microscopy, and the highly efficient photothermal ablation of prostatic tumors in vivo was demonstrated. This portfolio targeting strategy could be extended to various nanodrugs/agents to realize an accurate subcellular targeting efficiency for cancer treatments or cell detections.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Portfolio Targeting Strategy To Realize the Assembly and Membrane Fusion-Mediated Delivery of Gold Nanoparticles to Mitochondria for Enhanced NIR Photothermal Therapies

et al. 2020

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“…1,3-Propanediylbis(triphenylphosphonium) dibromide I, prepared initially as white powder by the reaction of triphenyl phosphine with 1,3-dibromopropane (m.p. : 349-354 • C by DSC method, 95% yield) [51] and then treated with an aqueous solution of ammonium peroxydisulfate in the ratio 1:1, white precipitate II was filtered and dried under a stream of air (Figure 1) (self-accelerating decomposition temperature SADT 200-205 • C by DSC method, 97% yield) Figure 2.…”

Section: Resultsmentioning

confidence: 99%

“…The product was air dried overnight (6.9 g, 95% yield, purity after recrystallization in hot water 99.7%), m.p. 349-353 • C (by DSC and DTA) [51] .…”

Section: Methodsmentioning

confidence: 99%

“…The structural parameters such as bond lengths, bond angles and dihedral (torsion) angles thermochemical parameters and were computed after optimization of structure (Table 2 and Table 3). The DFT calculation predicted energy and dipole moment for I, E (RB3LYP) -7334.05720641 Hartrees, Dipole moment = 16.9062 Debye [51] , while for II, E (RB3LYP) = -3589.09159282 Hartrees, Dipole moment 25.0194 Debye.…”

Section: Theoretical Dft Computationmentioning

confidence: 98%

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Synthesis, thermal properties, spectroscopic characterization and DFT computations of 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a new oxidative agent

2020

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Thermal properties and spectroscopic characterization of new synthesized 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a member of phosphonium persulfates were studied. 1 H, 13 C, 31 P NMR and FT-IR were used for structural characterization of the title salt. To study the thermal behavior of the salt DSC, TG and DTA methods were used. Self-accelerating decomposition temperature of anion determined 200-205 • C and decomposition point for organic moiety was recorded 340 • C by DSC method. The specific heat capacity of the salt was determined 1.32 to 1.96 j/g • C in comparison of sapphire disk between 30 to 160 • C. Theoretical DFT computations such as structural optimization, energy, charge distribution, HOMO-LUMO energy levels and thermochemical parameters were performed with the Gaussian 09 package software using B3LYP/6-31+G * level of theory. Theoretical calculations show HOMO-LUMO energy gap is 3.73 eV. Oxidation of several benzylic alcohols was performed by the persulfate salt in the water as a mild oxidative agent under reflux condition.

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“…1 1,3-bis(triphenylphosphino)propane dibromide (3a) A mixture of the triphenylphosphine (6.557 g, 25 mmol) and 1,3-dibromopropane (2.019 g, 10 mmol) in DMF (30 mL) was stirred and refluxed for 4 h. After reaction was complete, the reaction mixture was cooled and the crude white precipitate was filtered and washed with DMF (3 × 10 mL). The white powder was dried under stream of air and recrystallized in water as cubic shape crystals 3a (white solid, 6.901 g, 95%) [38].…”

Section: Synthesis and Characterizationsmentioning

confidence: 99%

Hydroxyl Group as the ‘Bridge’ to Enhance the Single-Molecule Conductance by Hyperconjugation

Lv,

Li,

Guo

et al. 2024

Molecules

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For designing single-molecule devices that have both conjugation systems and structural flexibility, a hyperconjugated molecule with a σ–π bond interaction is considered an ideal candidate. In the investigation of conductance at the single-molecule level, since few hyperconjugation systems have been involved, the strategy of building hyperconjugation systems and the mechanism of electron transport within this system remain unexplored. Based on the skipped-conjugated structure, we present a rational approach to construct a hyperconjugation molecule using a hydroxyl group, which serves as a bridge to interact with the conjugated fragments. The measurement of single-molecule conductance reveals a two-fold conductance enhancement of the hyperconjugation system having the ‘bridging’ hydroxyl group compared to hydroxyl-free derivatives. Theoretical studies demonstrate that the hydroxyl group in the hyperconjugation system connects the LUMO of the two conjugated fragments and opens a through-space channel for electron transport to enhance the conductance.

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Synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations and characterization of 1,3-propanediylbis(triphenylphosphonium) monotribromide as brominating agent of double bonds and phenolic rings

Cited by 6 publications

References 36 publications

Portfolio Targeting Strategy To Realize the Assembly and Membrane Fusion-Mediated Delivery of Gold Nanoparticles to Mitochondria for Enhanced NIR Photothermal Therapies

Portfolio Targeting Strategy To Realize the Assembly and Membrane Fusion-Mediated Delivery of Gold Nanoparticles to Mitochondria for Enhanced NIR Photothermal Therapies

Synthesis, thermal properties, spectroscopic characterization and DFT computations of 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a new oxidative agent

Hydroxyl Group as the ‘Bridge’ to Enhance the Single-Molecule Conductance by Hyperconjugation

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