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3,7-Dibromo-10H-phenothiazine

CAS Number 21667-32-3

Dibromo Monomers, Materials, Monomers


Product Code B4671-5g
Price £180 ex. VAT

Highly bioactive 10H-phenothiazine derivative

Widely used in DSSCs and energy devices, also for the preparation of hole selective self-assembled monolayers


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3,7-Dibromo-10H-phenothiazine (37DBrPTz), also known as thiodiphenylamine, is a symmetrically brominated derivate of 10H-phenothiazine. Phenothiazine related compounds are highly bioactive, and its derivatives chlorpromazine and promethazine are well known in the fields of psychiatry and allergy treatment. With a unique non-planar butterfly conformation, the non-conjugated 10H-phenothiazine structure can sufficiently suppress intra-molecular aggregation hence subdue the formation of excimers.

10H-phenothiazine derivatives are also widely used in dye-sensitized solar cells (DSSCs) and energy devices. The electron-rich nitrogen and sulfur atoms render 10H-phenothiazine a stronger donor character than other amines, i.e. triphenylamine, tetrahydroquinoline and carbazole. PTZAN||Zn battery based on 4,4-(10H-phenothiazine-3,7-diyl) bis (N,N-diphenylaniline) (PTZAN), showed excellent stability (2000cycles), high voltage (1.3V), high capacity (145mAhg1), and energy density of 187.2Whkg−1.

Most recently, 3,7-Dibromo-10H-phenothiazine has been engaged in the synthesis of self-assembled monolayer (SAM) materials such as Br-2EPT that was serving as the hole selective contact between anode and perovskite active layer. Perovskite solar cells using Br-2EPT as the interface achieved a power conversion efficiency (PCE) of up to 22.44% (certified 21.81%) with an average fill factor close to 81%, one of the top efficiencies reported to date for p-i-n PSCs.

General Information

CAS Number 21667-32-3
Chemical Formula C12H7Br2NS
Full Name 3,7-Dibromo-10H-phenothiazine
Molecular Weight 357.07 g/mol
Synonyms 37DBrPTz, Thiodiphenylamine, Dibenzothiazine, Dibenzoparathiazine
Classification or Family 10H-phenothiazine, Heterocyclic building blocks, SAMs

Chemical Structure

3,7-Dibromo-10H-phenothiazine (37DBrPTz) Chemical Structure, 21667-32-3

Product Details

Purity > 98%
Melting Point -
Appearance Pale green to beige powder

MSDS Documentation

3,7-dibromo-10H-phenothiazine - 21667-32-33,7-Dibromo-10H-phenothiazine MSDS Sheet

Literature and Reviews

  1. Synthesis and characterization of thermally cross-linkable hole injection polymer based on poly(10-alkylphenothiazine) for polymer light-emitting diode, M. Jung et al., Synth. Met., 159, 1928-1933 (2009); DOI: 10.1016/j.synthmet.2009.05.034.
  2. Molecular Tailoring of p–type Organics for Zinc Batteries with High Energy Density, X. Qiu et al., Angew. Chem. Int. Ed., 62 (30), e202304036 (2023); DOI: 10.1002/anie.202304036.
  3. Dual-channel D-(π-A)2 phenoxazine/phenothiazine dyes with an auxiliary N-alkoxy benzoic acid anchor for fabrication of dye-sensitized solar cells, Sol. Energy, 225, 173-183 (2021); DOI: 10.1016/j.solener.2021.07.030.
  4. Novel Phenothiazine-Based Self-Assembled Monolayer as a Hole Selective Contact for Highly Efficient and Stable p-i-n Perovskite Solar Cells, A. Ullah et al., Adv. Energy Mater., 2103175 (2021);DOI: DOI: 10.1002/aenm.202103175.
  5. Simple and robust phenoxazine phosphonic acid molecules as self-assembled hole selective contacts for high-performance inverted perovskite solar cells, Z. Li et al., Nanoscale, 15, 1676-1686 (2023); DOI: 10.1039/D2NR05677A.

     

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