Selectively functionalised at 2,7-postions with bromo groups only on one of the fluorenes, 2,7-dibromo-9,9′-spirobifluorene becomes a very useful intermediate for the synthesis of semiconducting molecules, polymers with a spirobifluorene core for applications in highly efficient OLEDs and perovksite solar cells.
2,7-Dibromo-9,9′-spirobifluorene is a double brominated derivative of 9,9′-spirobifluorene, only brominated at one of the joined fluorenes.
Bromos at 2,7-positions give 2,7-dibromo-9,9′-spirobifluorene ability to obtain derivatives with varying electronic characteristics and physical properties. The spirobifluorene core at 9-positon can provide certain characteristics like higher triplet
energy, elevated glass transition temperature, and thermal and chemical stabilities. It offers the prospect of controlling the molecular interaction of fluorene derivatives in the solid state by its sp3 carbon and twisted non-coplanar structure, preventing the close packing of molecules and generating amorphous glass materials with morphological stability. The connecting sp3 carbon also breaks the conjugation inside the molecule ending with a higher triplet energy. The twisted structure also gives more room for further modification at 2,7-positions.
2,7-Dibromo-9,9′-spirobifluorene can be prepared from 2,7-dribromo-9-fluorenone by reacting with a Grignard reagent of 2-bromobiphenyl. The most commonly known spirobifluorene based hole transport layer material is N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9,9′-spirobi[fluorene]-2,7-diamine (Spiro-NPB), and electron transport layer material 2,7-bis(diphenylphosphoryl)-9,9'-spirobifluorene (SPPO13, M2333A1).
|Molecular weight||474.19 g/mol|
|Classification / Family||Spirobifluorene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Melting point||Tm = 334-336 °C|
|Appearance||White to off-white powder/crystals|
2,7-Dibromo-9,9′-spirobifluorene MSDS Sheet
Literature and Reviews
Improved Synthesis of 2,2‘-Dibromo-9,9‘-spirobifluorene and Its 2,2‘-Bisdonor-7,7‘-bisacceptor-Substituted Fluorescent Derivatives, C. Chiang et al., Org. Lett. , 7, 17, 3717–3720 (2005); DOI: 10.1021/ol0513591.
Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives, F. Polo et al., J. Am. Chem. Soc., 134, 37, 15402–15409 (2012); DOI: 10.1021/ja3054018.
Red-Emitting Fluorenes as Efficient Emitting Hosts for Non-Doped, Organic Red-Light-Emitting Diodes, C. Chiang et al., Adv. Funct. Mater., 15 (2), 231-238 (2005); DOI: 10.1002/adfm.200400102.
Three Carbazole-Based Polymers as Potential Anodically Coloring Materials for High-Contrast Electrochromic Devices, Y. Su et al., Polymers, 9, 284 (2017); DOI: 10.3390/polym9070284.
Spirobifluorene Core-Based Novel Hole Transporting Materials for Red Phosphorescence OLEDs, R. Braveenth et al., Molecules, 22, 464 (2017); DOI: 10.3390/molecules22030464.
Spirobifluorene derivative: a pure blue emitter (CIEy 0.08) with high efficiency and thermal stability, X. Xing et al., J. Mater. Chem., 22, 15136-15140 (2012); DOI: 10.1039/c2jm32512h.
A Novel Electrochromic Polymer Synthesized through Electropolymerization of a New Donor-Acceptor Bipolar System, J. Natera et al., Macromolecules, 40, 4456-4463 (2007); DOI: 10.1021/ma070055m.
Bis-Sulfone- and Bis-Sulfoxide-Spirobifluorenes: Polar Acceptor Hosts with Tunable Solubilities for Blue-Phosphorescent Light-Emitting Devices, C. Ertl et al., Eur. J. Org. Chem., 2016 (11), 2037-2047 (2016); DOI: 10.1002/ejoc.201600247.
Bis(2,2-diphenylvinyl)spirobifluorene: An efficient and stable blue emitter for electroluminescence applications, F. Wu et al., Synth . Met., 151 (3), 2005, 285-292 (2005); DOI: 10.1016/j.synthmet.2005.06.003.
Highly fluorescent water soluble spirobifluorene dye with large Stokes shift: synthesis, characterization and bio-applications, F Schlüter et al., Chem. Commun., 54, 642-645 (2018); DOI: 10.1039/C7CC08761F.
- Synthesis, Structures, and Photoinduced Electron Transfer Reaction in the 9,9‘-Spirobifluorene-Bridged Bipolar Systems, K. Wong et al., J. Org. Chem., 71 (2), 456–465 (2006); DOI: 10.1021/jo0512047.
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