797316

1-{4-[1,2-Diphenyl-2-(p-tolyl)vinyl]phenyl}-1H-pyrrole-2,5-dione

• Synonym(s): TPE-Thiol
• Empirical Formula (Hill Notation): C₃₁H₂₃NO₂
• CAS Number: 1245606-71-6
• Molecular Weight: 441.52
• UNSPSC Code: 12352103
• PubChem Substance ID: 329768584
• NACRES: NA.23

Properties

• assay: 98%
• form: solid
• SMILES string: CC(C=C1)=CC=C1/C(C2=CC=CC=C2)=C(C3=CC=CC=C3)/C4=CC=C(N5C(C=CC5=O)=O)C=C4
• InChI: 1S/C31H23NO2/c1-22-12-14-25(15-13-22)30(23-8-4-2-5-9-23)31(24-10-6-3-7-11-24)26-16-18-27(19-17-26)32-28(33)20-21-29(32)34/h2-21H,1H3/b31-30+
• InChI key: CIMVFJJQFXGASK-NVQSTNCTSA-N

Description

General description

Aggregation-induced emission luminogens (AIEgen) were tailored to detect biological thiols. Maleimide is attached to the TPE core, giving TPE-Thiol.16. The reaction is inspired by the fast and efficient thiolene click reaction between maleimide and thiols, TPE-Thiol is not emissive in both solution and aggregated states, due to the photo-induced electron transfer from TPE to maleimide. However, reaction with thiol groups can interrupt the electron transfer process and turn-on the emission of TPE. TPE-Thiol can be used for labelling of protein carrying cysteine residues in the physiological media and poly(acrylamide) gel electrophoresis assays.

Application

TPE-Thiol is an aggregation-induced emission (AIE) material for the "Click" chemistry, with alkene and thio group detection.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable