2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene

CAS Number 128055-74-3

Chemistry Building Blocks, Materials, Monomers, Non-Heterocyclic Building Blocks

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene MSDS

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene CAS 128055-74-3

High-Purity 2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene

A very useful intermediate for the synthesis of semiconducting molecules, polymers with a spirobifluorene core for applications in highly efficient OLEDs and perovskite solar cells, i.e. Spiro-OMeTAD (Spiro-MeOTAD)

Specifications | MSDS | Literature and Reviews

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene (TBSBF), CAS number 128055-74-3, has a chemical structure of 9,9′-spirobifluorene core fully end-brominated benzene rings. 9,9′-spirobifluorene compounds have been known for their excellent thermal and chemical stabilities and facile solid amorphous films forming characteristics. The four bromos on each benzene ring enable further modification and extension of the core structure for more complex structures.

2,2′,7,7′-tetrabromo-9,9′-spirobifluorene can be prepared by brominating 9,9′-spirobifluorene using bromine as the oxidising agent and iron(III) chloride as the catalyst in quantitative yield. Yamamoto polymerization of 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene using bis-(1,5-cyclooctadiene)nickel(0) (Ni(COD)₂) as the catalyst gives thermally and chemically stable poly (SBF). Upon thermal treatment, the polymer has BET surface areas of ca. 2,000 m² g^-1.

An organic light-emitting device based on 2,2’,7,7’-tetrakis(pyren-1-yl)-9,9’-spirobifluorene (TPSBF) which was synthesised from 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene as one of the starting materials, exhibited a broad-spectrum white emission showing a maximum luminescence and current efficiency of 57 680 cd m^-2 and 6.51 cd A^-1, with the following configuration: ITO (170 nm)/2-TNATA (15 nm)/NPB (65 nm)/TPSBF (50 nm)/Alq3 (30 nm)/LiF (0.8 nm)/Al (200 nm).

Spirobifluorene building block

For the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Capped with bromides

for facile coupling reactions

High purity

>99% Purity

General Information

CAS Number	128055-74-3
Chemical Formula	C₂₅H₁₂Br₄
Full Name	2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene
Molecular Weight	631.98 g/mol
Synonyms	2,2′,7,7′-Tetrabromo-9,9′-spirobi[9H-fluorene], TBSBF
Classification / Family	Spirobifluorene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>99% (HPLC)
Melting Point	T_m = 395 °C - 400 °C
Appearance	White to off-white powder/crystals

MSDS Documentation

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene MSDS Sheet

Literature and Reviews

Fluorinated 9,9'-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices, C. Li et al., J. Mater. Chem. C, 1, 2183-2192 (2013); DOI: 10.1039/C3TC00466J.
Molecular Glass Resists Based on 9,9′-Spirobifluorene Derivatives: Pendant Effect and Comprehensive Evaluation in Extreme Ultraviolet Lithography, J. Chen et al., ACS Appl. Polym. Mater., 1 (3), 526–534 (2019); DOI: 10.1021/acsapm.8b00235.
A Spirobifluorene Derivative as a Single-Emitting Component for a Highly Efficient White Organic Electroluminescent Device, H. Wen et al., Chempluschem, 78(10), 1288-1295 (2013); DOI: 10.1002/cplu.201300088.

Sustainable, Efficient, and Scalable Preparation of Pure and Performing Spiro-OMeTAD for Perovskite Solar Cells, S. Mattiello et al., ACS Sustainable Chem. Eng., 10, 4750−4757 (2022); DOI: 10.1021/acssuschemeng.2c00493.
Thermally Enhancing the Surface Areas of Yamamoto-Derived Porous Organic Polymers, B. Hauser et al., Chem. Mater., 25, 1, 12–16 (2013); DOI: 10.1021/cm3022566.