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CAS 2052287-45-1

(E)-4,4'-Bis(octyloxy)-3-methylazobenzene TCI B6252

(E)-4,4'-Bis(octyloxy)-3-methylazobenzene TCI B6252

Chemical Identity

Other names
(E)-1-[3-Methyl-4-(octyloxy)phenyl]-2-[4-(octyloxy)phenyl]diazene
CAS No.
2052287-45-1
Formula
C29H44N2O2
Molecular weight
452.68 g/mol
Purity
>95.0%(HPLC)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
(3-methyl-4-octoxyphenyl)-(4-octoxyphenyl)diazene
SMILES
CCCCCCCCOC1=CC=C(C=C1)N=NC2=CC(=C(C=C2)OCCCCCCCC)C
InChIKey
LCCCZULLTPSQIV-UHFFFAOYSA-N
PubChem
CID 172994745
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(E)-4,4'-Bis(octyloxy)-3-methylazobenzene is a photochromic dye belonging to the azobenzene family, built from two benzene rings joined by a nitrogen-nitrogen double bond, carrying long octyloxy chains at both ends and a methyl group as an additional substituent. Compounds of this type play an important role in materials science laboratories as molecular units that change shape when illuminated. The change is reversible, which turns the molecule into a molecular switch that allows researchers to control the properties of a material simply by adjusting the illumination, without adding any chemical reagent to the system.

The property that makes this compound a preferred choice is the isomerisation between the elongated trans form and the bent cis form. This change in shape alters the molecular dimensions, the dipole moment, and the ability of the molecule to organise itself into ordered arrangements, which in turn can modify the optical properties, the solubility, and the phase order of a material. The long octyloxy chains at both ends impart amphiphilic character and a tendency to form ordered assemblies, a feature that is especially useful in liquid crystal research and in ordered thin films. The methyl substituent contributes further to how the molecules pack and respond.

In Indonesian laboratories, materials of this class are typically handled in university and institutional research groups working on photonic and optical materials, where they are used at small scale for exploratory synthesis, film preparation, and optical characterisation. They are normally purchased in research quantities rather than bulk, weighed out in a fume hood or on a clean bench, and dissolved in organic solvents for spectroscopic measurement or for deposition onto substrates.

  • Photoswitching and molecular switch studies, because the reversible trans-to-cis isomerisation lets researchers toggle molecular shape with light alone, without introducing additional chemical reagents into the system.
  • Liquid crystal research, since the long octyloxy chains at both ends promote ordered molecular assemblies whose phase order can be perturbed reversibly by controlled illumination of the sample.
  • Ordered thin film preparation, where the amphiphilic character conferred by the terminal octyloxy chains supports the formation of regular layered arrangements on substrates for subsequent optical study.
  • Light-controlled optical property investigations, because the shape change accompanying isomerisation modifies the optical response of the host material and allows tuning purely through the illumination conditions.
  • Solubility and dipole moment studies, as the trans and cis forms differ in dimensions and dipole moment, giving a convenient model system for correlating molecular geometry with bulk behaviour.

Brand TCI
CAS number 2052287-45-1
Molecular formula —
Purity —
Category Materials Science > Photonic Materials and Optical Materials > Photochromic Dyes
Pack sizes available in standard research quantities as supplied by the manufacturer
Physical form —
Storage keep in a tightly closed container, protected from light
  • Product code: B6252

Store the material in its original tightly closed container in a cool, dry place, protected from light, since photochromic dyes respond to illumination and uncontrolled light exposure can shift the isomer distribution before use. Amber glass or otherwise light-shielded containers are suitable; keep the container closed when not in use to limit moisture uptake. Handle the compound in a fume hood or a well-ventilated area, wearing gloves, safety glasses, and a laboratory coat, and avoid generating or inhaling dust when weighing. Use clean, dry spatulas and glassware to prevent contamination. Consult the manufacturer's safety data sheet before use and dispose of residues and contaminated materials in accordance with applicable laboratory waste procedures.

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