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P14831

Sigma-Aldrich

Phenothiazine

≥98%

Synonym(s):

Dibenzo-1,4-thiazine, Thiodiphenylamine, 10H-Phenothiazine

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About This Item

Empirical Formula (Hill Notation):
C12H9NS
CAS Number:
92-84-2
Molecular Weight:
199.27
Beilstein:
143237
EC Number:
202-196-5
MDL number:
MFCD00005015
UNSPSC Code:
12352103
PubChem Substance ID:
24898205
NACRES:
NA.23

Assay

≥98%

bp

371 °C (lit.)

mp

182-187 °C (lit.)

SMILES string

N1c2ccccc2Sc3ccccc13

InChI

1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

InChI key

WJFKNYWRSNBZNX-UHFFFAOYSA-N

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General description

Phenothiazine is a versatile building block that can be easily functionalized as it possesses multiple modification sites. Its unique butterfly configuration and electron-rich character are beneficial for its potential use in optoelectronic applications. As it can undergo fast and reversible electron transfer reactions, it is widely used as photoactive material in organic light-emitting devices and solar cells.

Application

Phenothiazine can be used in the following applications:
  • It can be connected to carbazole by C-N linkage to increase the hole mobility and thermal stability in organic light-emitting devices.
  • Used in the fabrication of CMA-based (Carbene-Metal-Amide) white light-emitting OLED.
  • It is used as a starting material in the synthesis of dialdehyde monomer. A conjugated copolymer is prepared using this dialdehyde monomer, which is applicable as an emitting layer in PLED.
  • Used as a building block in the synthesis of conjugated dendrimers, for the development of light-emitting devices.

Signal Word

Warning

Hazard Statements

H302,H317,H373,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Sens. 1 - STOT RE 2 Oral

Target Organs

Blood

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rajendra Kumar Konidena et al.
The Journal of organic chemistry, 80(11), 5812-5823 (2015-05-08)
A series of thienylphenothiazine decorated carbazoles were synthesized and characterized by optical, electrochemical, thermal, and theoretical investigations. Absorption spectra of the compounds are influenced by the substitution pattern and chromophore number density. Compounds containing 2,7-substitution exhibited red-shifted absorption, while the
Synthesis of p-type conjugated dendrimers bearing phenothiazine moiety at the periphery and their light-emitting device characterization
Dong Hoon Choi, et al.
Synthetic Metals, 157(8), 332-335 (2007)
Structure-induced optoelectronic properties of phenothiazine-based materials
Revoju, et al.
Journal of Material Chemistry C, 8(44), 15486-15506 (2020)
Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A, 237, 419-419 (1993)
Alexander S Romanov et al.
Chemical science, 11(2), 435-446 (2020-03-20)
Conformationally flexible "Carbene-Metal-Amide" (CMA) complexes of copper and gold have been developed based on a combination of sterically hindered cyclic (alkyl)(amino)carbene (CAAC) and 6- and 7-ring heterocyclic amide ligands. These complexes show photoemissions across the visible spectrum with PL quantum
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