Structure via PubChem · Public domain (PubChem)
Triphenylethene
Sign in to saveAlso known as benzilidenediphenylmethane, triphenylethylene
Triphenylethylene (TPE) is the organic compound with the formula . It is a colorless solid. ==Synthesis and reactions== The compound is prepared in two steps from benzophenone via the intermediacy of 1,2,2-triphenylethanol. Triphenylethylene reacts with iodine to give 9-phenylphenanthroline. Epoxidation gives the chiral oxirane.
Chemical data
- Formula
- C20H16
- Molecular weight
- 256.3 g/mol
- IUPAC name
- 1,2-diphenylethenylbenzene
- SMILES
- C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
- InChIKey
- MKYQPGPNVYRMHI-UHFFFAOYSA-N
- XLogP
- 6.1
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
19 papers- A Solid-State Fluorescence Switch Based on Triphenylethene-Functionalized Dithienylethene With Aggregation-Induced Emission.Frontiers in chemistry · 2021
- Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme.Journal of enzyme inhibition and medicinal chemistry · 2002
- Intrinsic hydroquinone-functionalized aggregation-induced emission core shows redox and pH sensitivity.Communications chemistry · 2021
- Bioactive Peptide-Mimicking Polymer Nanoparticles for Bacteria Imaging and Chemo/Immunotherapy of Intracellular Infection.ACS macro letters · 2023
- AIE-enabled transfection-free identification and isolation of viable cell subpopulations differing in the level of autophagy.Autophagy · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 256.125
Show 4 more facts
- canonical SMILES
- C1=CC=C(C=C1)C=C(C2=CC=CC=C2)C3=CC=CC=C3
- chemical formula
- C₂₀H₁₆
- subject has role
- estrogen antagonist
- Commons category
- Triphenylethene
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Synthesis and reactions
- Bioactivity
- See also
- References
Triphenylethylene (TPE) is the organic compound with the formula . It is a colorless solid. ==Synthesis and reactions== The compound is prepared in two steps from benzophenone via the intermediacy of 1,2,2-triphenylethanol. Triphenylethylene reacts with iodine to give 9-phenylphenanthroline. Epoxidation gives the chiral oxirane.
==Bioactivity== Triphenylethylene possesses weak estrogenic activity. Its estrogenic effects were discovered in 1937. TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is a member of the stilbestrol group of nonsteroidal estrogens.
Excerpted from Wikipedia’s “Triphenylethene” article, available under the CC BY-SA 4.0 licence.