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CAS Number 291279-14-6

Carbaldehyde Monomers, Chemistry Building Blocks, COF Ligands, Materials, Porous Organic Frameworks

Product Code B3811-1g
Price $63 ex. VAT

Covalent Organic Frameworks (COFs) Triphenylamine Ligand

A formyl functional ligand linker for COFs in application of aggregation induced emission (AIE) two-photon fluorescent probe

Specifications | MSDS | Literature and Reviews

5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde (DPAPTA), CAS number 291279-14-6, is consisted of a triphenylamine core with a 2-carbaldehydethiophene attached to one of the phenyl rings. The aldehyde functional group is ideal to form double bond π-bridges with amines via condensation reaction.

Derived from 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde, aggregation induced emission (AIE) two-photon fluorescent probe AIETP demonstrated efficient brain vasculature imaging with high brightness and improved photostability. AIETP NPs showed excellent two-photon cross section and in vivo stability apart from demonstrating great cell permeability and biocompatibility.

A mitochondria-anchoring photosensitizer, TTVPHE, also derived from 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde with AIE characteristics for efficient ablation of extrahepatic cholangiocarcinoma cells. The TTVPHE probe showed great advantage for fast cell penetration and selective mitochondria-targeting abilities, and excellent reactive oxygen species (ROS) generation under the visible light irradiation.

Triphenyl amine-thiophene conjugated with benzothiazole derivative fluorescent probe TP-1, showed a visible colour change from dark yellow to colourless and subsequently the fluorescence intensity increase after the addition of the cyanide anions in the linear range of 1 – 100 μM. The limit of detection for cyanide ions by the probe TP-1 was found to be 4.24 x 10−8 M.

TTVP, a D–A type compound comprising triphenylamine and thiophene fragments (D and π-bridge) and a carbon–carbon double bond showed AIE features, good water-solubility and intense emission in the NIR region. This AIE luminogen (AIEgen) can specifically light up the cell membrane without the involvement of a washing procedure. The staining process is ultrafast and easy-to-operate, performed by simply shaking the culture with cells at room temperature for only a few seconds after the addition of the AIEgen.

MOF and COF ligands

MOF and COF ligands

Aldehyde ligand for end-capping COF networks

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High purity 291279-14-6

High purity

>98% High purity

Facile reactions

Facile reactions

Aldehyde possesses excellent reactivity

General Information

CAS Number 291279-14-6
Chemical Formula C23H17NOS
Full Name 5-(4-(Diphenylamino)phenyl)thiophene-2-carbaldehyde
Molecular Weight 355.45 g/mol
Synonyms DPAPTA, 2-Thiophenecarboxaldehyde, 5-[4-(diphenylamino)phenyl]-
Classification / Family Triphenylamine, COF ligands, Aggregation induced emission (AIE)

Chemical Structure

291279-14-6 - 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde chemical structure
5-(4-(Diphenylamino)phenyl)thiophene-2-carbaldehyde (DPAPTA) Chemical Structure, 291279-14-6

Product Details

Purity >98%
Melting Point N/A
Appearance Yellow to orange powder/crystals

MSDS Documentation

291279-14-6 - 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde5-(4-(Diphenylamino)phenyl)thiophene-2-carbaldehyde MSDS Sheet

Literature and Reviews

  1. AIE-active two-photon fluorescent nanoprobe with NIR-II light excitability for highly efficient deep brain vasculature imaging, S. Samanta et al., Theranostics, 11(5), 2137–2148 (2021); DOI: 10.7150/thno.53780.
  2. Mitochondria-anchoring and AIE-active photosensitizer for self-monitored cholangiocarcinoma therapy, T. Zhou et al., Mater. Chem. Front., 4, 3201-3208 (2020); DOI: 10.1039/D0QM00503G.
  3. Tuning the HOMO and LUMO Energy Levels of Organic Chromophores for Dye Sensitized Solar Cells, D. Hagberg et al., J. Org. Chem., 72 (25), 9550–9556 (2007); DOI: 10.1021/jo701592x.
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