Chemical Structure and Physical Properties

(E)-1,2-Bis(4-tert-butylphenyl)ethene belongs to the stilbene family of compounds, characterized by a central ethylene (CH=CH) bridge connecting two aromatic rings in a trans (E) geometry. The molecular formula is C₂₂H₂₈, giving a molecular weight of approximately 296.46 g/mol. Each phenyl ring carries a tert-butyl group at the para position, imparting steric bulk that promotes solubility in common organic solvents such as dichloromethane, toluene, and tetrahydrofuran, while discouraging tight crystalline packing and π–π stacking aggregation.

The extended π-conjugation across the stilbene backbone endows this compound with characteristic UV absorption in the near-UV region and blue-shifted fluorescence emission relative to unsubstituted stilbene. The rigid planar backbone, combined with the electron-donating character of the alkyl substituents, influences both the HOMO–LUMO gap and the photoluminescence quantum yield, making this compound of interest for photophysical characterization studies.

Synthesis and Handling

Symmetric diarylethylenes of this type are commonly accessed via Wittig or Horner–Wadsworth–Emmons olefination reactions, or through McMurry coupling of the corresponding aldehyde precursor (4-tert-butylbenzaldehyde). The E-selective nature of these routes, particularly the Horner–Wadsworth–Emmons approach, affords the thermodynamically more stable trans isomer predominantly. The high symmetry of the molecule simplifies purification, typically achieved by recrystallization from ethanol or column chromatography on silica gel.

As a solid organic compound, (E)-1,2-Bis(4-tert-butylphenyl)ethene should be stored in a cool, dry location away from light to minimize potential photoisomerization to the Z-isomer. Standard laboratory personal protective equipment is recommended when handling the material. Researchers should consult the Safety Data Sheet (SDS) for specific hazard classifications and first-aid measures prior to use.

Research Applications

(E)-1,2-Bis(4-tert-butylphenyl)ethene finds application across several research domains:

• Organic electronics and optoelectronics: Stilbene derivatives serve as model chromophores and active-layer components in studies of organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic photovoltaics. The tert-butyl groups modulate film morphology and energy levels.
• Fluorescence and photophysics studies: The compound is useful as a reference fluorophore or host material for investigating energy transfer, singlet-state dynamics, and photoisomerization mechanisms in conjugated organic systems.
• Supramolecular chemistry: The well-defined geometry and hydrophobic periphery of this stilbene derivative facilitate its use in host–guest chemistry, self-assembly investigations, and the construction of supramolecular architectures.
• Synthetic intermediates: The terminal olefin unit can participate in further functionalization reactions, making this compound a potential building block for more complex π-conjugated materials.

Ordering and Availability from Aladdin Scientific

(E)-1,2-Bis(4-tert-butylphenyl)ethene is available from Aladdin Scientific under SKU B1539856. Researchers are encouraged to confirm current stock levels, available pack sizes, purity specifications, and pricing through the Aladdin Scientific website or by contacting customer service directly. Bulk quantities and custom specifications may be available upon request.

When placing an order, please reference the SKU to ensure accurate fulfillment. For questions regarding certificates of analysis (CoA), safety data sheets (SDS), or regulatory documentation, the Aladdin Scientific technical support team is available to assist.