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

CAS Number 128055-74-3

Chemistry Building Blocks, Monomers, Non-Heterocyclic Building Blocks

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene CAS 128055-74-3
Product Code B1011-10g
Price £185 ex. VAT
£ GBP

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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)

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).

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

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

Product Details

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

MSDS Documentation

2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene2,2′,7,7′-Tetrabromo-9,9′-spirobifluorene MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
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