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2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride

CAS Number 83204-68-6

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers

Product Code B3211-LT-1g
Price $119 ex. VAT

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2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride (NTCDA-2Br)

A building block for the synthesis of n-type semiconducting polymers and dyes for polymer solar cells, OFETs and bioimaging applications

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride (NTCDA-2Br) is a symmetric naphthalene derivative with adjacent carboxylic acids forming anhydride on both ends of the structure. It is a precursor to naphthalene diimides (NDIs) which are used as active layer materials in organic solar cells, field-effect transistors.

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride possesses aromatic planar conjugated structure and is favourable for good charge transport. Materials composed of naphthalene-1,4,5,8-tetracarboxylic dianhydride (NTDCA) or naphthalene-diimides (NDIs) have an excellent combination of redox, electrical, optical and thermal properties with high moisture and oxygen resistance.

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride on its own could be used as cathode interlayer materials for efficient electron extraction.

General Information

CAS Number 83204-68-6
Chemical Formula C14H2Br2O6
Full Name 2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride
Molecular Weight 425.97 g/mol
Synonyms 4,9-Dibromoisochromeno[6,5,4-def]isochromene1,3,6,8-tetraone, NTCDA-2Br
Classification / Family Naphthalenes, Monomers, Electron transport layer materials

Chemical Structure

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride, 83204-68-6 chemical structure
2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride, CAS 83204-68-6

Product Details

Purity >98% (GC)
Melting Point 350 °C
Appearance Yellow to dark green powder/crystals

MSDS Documentation

2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride MSDS2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride MSDS Sheet

Literature and Reviews

  1. A Balanced Face-On to Edge-On Texture Ratio in Naphthalene Diimide-Based Polymers with Hybrid Siloxane Chains Directs Highly Efficient Electron Transport, Y. Kim et al., Macromolecules 48 (15), 5179–5187 (2015); DOI: 10.1021/acs.macromol.5b01012.
  2. The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers, I. Maria et al., Adv. Funct. Mater., 31, 2008718 (2021); DOI: 10.1002/adfm.202008718.
  3. The synthesis of novel core-substituted naphthalene diimides via Suzuki cross-coupling and their properties, S. Bhosale et al., New J. Chem., 33, 2409-2413 (2009); DOI: 10.1039/B9NJ00476A.
  4. Rod-like oligomers incorporating 2,6-dialkylamino core-substituted naphthalene diimide as acceptors for organic photovoltaic, R. Fernando et al., Org. Electron., 14 (6), 683-1692 (2013); DOI: 10.1016/j.orgel.2013.03.039.
  5. Improved Performance of Solution-Processed n‑Type Organic Field-Effect Transistors by Regulating the Intermolecular Interactions and Crystalline Domains on Macroscopic Scale, S. Vasimalla et al., Chem. Mater., 26, 4030−4037 (2014); DOI: 10.1021/cm501780p.

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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