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

CAS Number 291279-14-6

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

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

5-(4-(Diphenylamino)phenyl)thiophene-2-carbaldehyde CAS 291279-14-6

Covalent Organic Frameworks (COFs) Triphenylamine Ligand

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

Overview
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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

Aldehyde ligand for end-capping COF networks

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

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

Product Details

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

MSDS Documentation

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

Literature and Reviews

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.
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.
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.
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.
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.
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.

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