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797316

Sigma-Aldrich

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

Synonym(s):

TPE-Thiol

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About This Item

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

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Simple Biosensor with High Selectivity and Sensitivity: Thiol-Specific Biomolecular Probing and Intracellular Imaging by AIE Fluorogen on a TLC Plate through a Thiol?Ene Click Mechanism
Yang Liu, Yong Yu, Jacky W. Y. Lam, Yuning Hong, Mahtab Faisal, et al
Chemistry (Weinheim An Der Bergstrasse, Germany), 16(28), 8433-8438 (2010)

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