186605-76-5

Usage

Uses

Used in the Preparation of Dendrimers:
3,5-BIS[3,5-BIS(METHOXYCARBONYL)PHENOXYMETHYL]PHENOL is used as a monomer in the synthesis of dendrimers for their unique properties. Dendrimers are highly branched, synthetic macromolecules with a well-defined, tree-like structure. They are employed in various fields, including drug delivery, nanotechnology, and materials science, due to their precise control over size, shape, and surface chemistry.
Used in the Formation of Dendritic Metallogels:
3,5-BIS[3,5-BIS(METHOXYCARBONYL)PHENOXYMETHYL]PHENOL is utilized as a component in the creation of dendritic metallogels, which are a class of soft materials that combine the properties of dendrimers with metal ions to form a gel-like substance. These metallogels have potential applications in areas such as catalysis, sensing, and the development of new materials with tailored properties.

InChI:InChI=1/C28H26O11/c1-34-25(30)18-8-19(26(31)35-2)11-23(10-18)38-14-16-5-17(7-22(29)6-16)15-39-24-12-20(27(32)36-3)9-21(13-24)28(33)37-4/h5-13,29H,14-15H2,1-4H3

Upstream product

• 186605-72-1 1-tert-butyldimethylsiloxy-3,5-bis[3,5-bis(methoxycarbonyl)phenoxymethyl]benzene 
• 1161868-09-2 C₃₀H₃₀O₁₂ 
• 13036-02-7 Dimethyl 5-hydroxyisophthalate 
• 153707-56-3 3,5-bis(hydroxymethyl)phenol 
• 221648-03-9 1,3-bis(hydroxymethyl)-5-(methoxymethoxy)benzene 
• 848498-23-7 dimethyl 5-(methoxymethoxy)isophthalate 
• 219965-98-7 5-(tert-butyldimethylsilyloxy)isophthalic acid 
• 182629-24-9 dimethyl 5-{[(1,1-dimethylethyl)dimethylsilyl]oxy}benzene-1,3-dicarboxylate 
• 182629-25-0 5-{[(1,1-dimethylethyl)dimethylsilyl]oxy}benzene-1,3-dimethanol 
• 347307-84-0 3,5-bis(bromomethyl)phenyl benzoate 
• 108-68-9 3,5-Dimethylphenol 
• 5554-28-9 (3,5-Dimethylphenyl)benzoat 
• 347307-87-3 3,5-3,5-(dimethoxycarbonylphenoxymethyl)phenyl benzoate 

Downstream Products

• 347307-90-8 3,5-bis-[3,5-3,5-(dimethoxycarbonylphenoxymethyl)phenoxymethyl]phenyl benzoate 
• 1587638-85-4 C₃₄H₃₁NO₁₁ 

Relevant academic research and scientific papers

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico-Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

Sulfanyl porphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The presence of a dendrimeric periphery enhanced the spectral properties of the porphyrazines studied. The singlet-oxygen-generation quantum yield of the obtained macrocycles ranged from 0.02 to 0.20 and was strongly dependent on the symmetry of the compounds and the terminal groups of the dendritic outer shell. The in vitro biological effects of three most promising tribenzoporphyrazines were examined; the results indicated their potential as photosensitizers for photodynamic therapy (PDT) against two oral squamous cell carcinoma cell lines derived from the tongue. The highest photocytotoxicity was found for sulfanyl tribenzoporphyrazine that possessed 4-[3,5-di(hydroxymethyl)phenoxy]butyl substituents with nanomolar IC50 values at 10 and 42 nm against CAL 27 and HSC-3 cell lines, respectively. Topic of cancer: Sulfanyl porphyrazines and tribenzoporphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The in vitro biological effects of three most promising tribenzoporphyrazines were examined and found to exhibit nanomolar IC50 values (see figure).

A systematic study of peripherally multiple aromatic ester-functionalized poly(benzyl ether) dendrons for the fabrication of organogels: Structure-property relationships and thixotropic property

A new class of peripherally multiple aromatic ester-functionalized poly(benzyl ether) dendrons and/or dendrimers with different focal point substituents, surface groups, interior structures, as well as different generations have been synthesized and their structure-property relationships with respect to their gelation ability have been investigated systematically. Most of these dendrons are able to gel organic solvents over a wide polarity range. Evident dendritic effects were observed not only in gelation capability but also in thermotropic, morphological, and rheological characterizations. It was disclosed that subtle changes in peripheral ester functionalities and interior dendritic structures affected the gelation behavior of the dendrons significantly. Among all the dendrons studied, the second- and third-generation dendrons G0G2-Me and G0G3-Me with dimethyl isophthalates (DMIP) as peripheral groups exhibited the best capability in gelation, and stable gels were formed in more than 22 aromatic and polar organic solvents. The lowest critical gelation concentration (CGC) reached 2.0 mg mL-1, indicating that approximately 1.35×104 solvent molecules could be entrapped by one dendritic molecule. Further study on driving forces in gel formation was carried out by using a combination of single-crystal/powder X-ray diffraction (XRD) analysis and concentration- dependent (CD)/temperature-dependent (TD) 1H NMR spectroscopy. The results obtained from these experiments revealed that the multiple π-π stacking of extended π-systems due to the peripheral DMIP rings, cooperatively assisted by non-conventional hydrogen-bonding, is the key contributor in the formation of the highly ordered supramolecular and fibrillar network. In addition, these dendritic organogels exhibited unexpected thixotropic-responsive properties, which make them promising candidates with potential applications in the field of intelligent soft materials. s

Peripherally dimethyl isophthalate-functionalized poly(benzyl ether) dendrons: A new kind of unprecedented highly efficient organogelators

(Figure Presented) A series of poly(benzyl ether) dendrons, up to the fourth generation, decorated in their periphery with dimethyl esters were divergently synthesized and fully characterized. These dendrons were found to be unprecedented highly efficient

Dendritic effects in catalysis by Pd complexes of bidentate phosphines on a dendronized support: Heck vs. carbonylation reactions

Bidentate phosphine ligands have been prepared on polystyrene beads modified with polyether dendron spacers. When complexed to Pd0, these systems exhibited a negative dendritic effect on Heck catalysis (contrary to the analogous monodentate phosphine systems), but mostly a positive influence on carbonylation. This opposite influence of the dendronization falls into line with other differences in the optimal ligand structure for the two reactions. The negative effect on the Heck catalysis with bidentate phosphines may indicate that dendrimer-induced reduction in the cross-linking upon Pd complexation is responsible for the positive effect in the corresponding monodentate phosphine systems.

Synthesis of poly(aryl benzyl ether) dendrimers on solid support

Dendronized supports, combining core Wang resin and poly(aryl benzyl ether) dendrons, were prepared using a novel route. Employing a dimethyl 5-hydroxyisophthalate module and a Mitsunobu condensation/ester reduction iterative sequence, the dendrimer was cleanly and efficiently prepared to the third generation. The synthesis was monitored using gel-phase 13C NMR and acidolytic cleavage, followed by 1H NMR. Gel-phase NMR and swelling experiments demonstrated that the behavior of the dendronized resins in various solvents is strongly influenced by the peripheral functional groups. Synthesis of a cinnamate derivative (via Mitsunobu and Heck reactions) and of a tripeptide demonstrated suitability of the dendronized support for solid-phase synthesis.

New simple convergent synthetic method for benzyl aryl ether dendritic structures

Phenolic benzyl aryl ether based dendrons with an ester periphery are easily prepared by convergent strategy through hydroxy substituted methyl benzoates and easily attainable benzoyl protected 3,5-bis(bromomethyl)phenol. The dendrons obtained can afford dendronized styrenes.

Methoxycarbonyl-Terminated Dendrons via the Mitsunobu Reaction: An Easy Way to Functionalized Hyperbranched Building Blocks

Methoxycarbonyl-terminated dendrons can be easily prepared up to the third generation by a convergent approach using the Mitsunobu reaction as the bond-forming step.The advantages of this procedure are that the transformation of the alcohol moiety to a leaving group and its nucleophilic displacement are performed in one pot under mild conditions.

Linked bis-isophthalic acid derivatives as building blocks in the design of self-assembling structures

In this paper we show that linked bis-isophthalic acid derivatives form ordered molecular structures in the solid state. The key organizing interactions are hydrogen bonds between the isophthalate carboxylic acid substituents on adjacent molecules or to methanol solvent. NMR investigations suggest that alternative aggregates form in solution.