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

CAS Number 83204-68-6

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

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

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

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

Overview
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2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic dianhydride (NTCDA-2Br, CAS number 83204-68-6) 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

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 MSDS Sheet

Literature and Reviews

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.
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.
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.
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.
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.

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