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5-(4-(Diphenylamino)phenyl)thiophene-2-carbaldehyde

CAS Number 291279-14-6

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


Product Code B3811-1g
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Covalent Organic Frameworks (COFs) Triphenylamine Ligand

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


5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde (DPAPTA) 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 C33H17NOS
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.
  4. Enhancing the efficiency of solution-processable bulk-heterojunction devices via a three-dimensional molecular architecture comprising triphenylamine and cyanopyridone, R. Hangarge et al., Dyes Pigms., 137, 126-134 (2017); DOI: 10.1016/j.dyepig.2016.10.008.
  5. Triphenylamine-thiophene dyad as a Chemodosimeter for specific recognition of cyanide ions in aqueous solutions, Y. Zhao et al., Dyes Pigms., 183, 108713 (2020); DOI: 10.1016/j.dyepig.2020.108713.
  6. Rational design of a water-soluble NIR AIEgen, and its application in ultrafast wash-free cellular imaging and photodynamic cancer cell ablation, D. Wang et al., Chem. Sci., 9, 3685-3693 (2018); DOI: 10.1039/C7SC04963C.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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