9,9′-Spirobifluorene

CAS Number 159-66-0

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

High-Purity 9,9′-Spirobifluorene

With great thermal and chemical stabilities, spiro compounds with 9,9′-spirobifluorene core of inherent rigid structure have attracted great attention as organic functional materials.

Specifications | MSDS | Literature and Reviews

Structurally, 9,9′-Spirobifluorene (SBF), CAS number 159-66-0, can be considered as two fluorenes joined together at 9,9'-positions. 9,9'-Spirobifluorene has received considerable interest for organic electronics, featuring a sp³-hybridized carbon with two perpendicularly aligned π systems. The two fluorene units through a shared spiro-carbon are hence maintained in orthogonal planes.

Spiro compounds with 9,9′-spirobifluorene core of inherent rigid structure thus have attracted great attention as organic functional materials for their specific physical properties, such as high glass transition temperatures, good solubility and their amorphous nature. The prominent spiro-structure can also very effectively suppresses excimer formation frequently observed in the solid state of many fluorescent dyes. Particularly, spirobifluorenes are known for their excellent thermal and chemical stabilities, high quantum efficiencies, as well as nondispersive ambipolar carrier transporting properties.

9,9'-spirobifluorene-based conjugated microporous organic polymers (COPs) can be obtained directly from unsubstituted spirobifluorene using an inexpensive FeCl₃ mediator via either oxidative polymerization, Friedel-Crafts polymerization, or competitive oxidative/Friedel-Crafts polymerization. Those COPs show large surface areas (940 – 1980 m²g^-1) and high micropore volumes (0.5 – 0.9 cm³g^-1).

General Information

CAS Number	159-66-0
Chemical Formula	C₂₅H₁₆
Full Name	9,9′-Spirobifluorene
Molecular Weight	316.39 g/mol
Synonyms	9,9′-Spirobi[9H-fluorene], SBF
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 = 202 °C
Appearance	White powder/crystals

MSDS Documentation

9,9′-Spirobifluorene MSDS Sheet

Literature and Reviews

Hole Mobilities of 2,7- and 2,2′-Disubstituted 9,9′-Spirobifluorene-Based Triaryldiamines and Their Application as Hole Transport Materials in OLEDs, Y. Liao et al., Chem. Mater. , 19, 6350–6357 (2007); DOI: 10.1021/cm702230.
2-Substituted vs 4-substituted-9,90-spirobifluorene host materials for green and blue phosphorescent OLEDs: a structureeproperty relationship study, S. Thiery et al., Tetrahedorn, 70, 6337-6351 (2014); DOI: 10.1016/j.tet.2014.05.081.
Synthesis, Structures, and Photoinduced Electron Transfer Reaction in the 9,9′-Spirobifluorene-Bridged Bipolar Systems, K. Wong et al., J. Org. Chem. 2006, 71, 456-465 (2006); DOI: 10.1021/jo0512047.

Fluorinated 9,9′-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices, Z. Li et al., J. Mater. Chem. C, 1, 2183-2192 (2013); 10.1039/C3TC00466J.
White organic light-emitting diodes based on 2,7-bis(2,2-diphenylvinyl)-9,9′-spirobifluorene: Improvement in operational lifetime, C. Chuen et al., Appl. Phys. Lett., 85, 4609 (2004); DOI: 10.1063/1.1824178.
Bis(diphenylamino)-9,9′-spirobifluorene functionalized Ir(iii) complex: a conceptual design en route to a three-in-one system possessing emitting core and electron and hole transport peripherals, H. Chen et al.,J. Mater. Chem., 21, 768-774 (2011); DOI: 10.1039/C0JM02097D.
9,9′-Spirobifluorene and 4-phenyl-9,9′-spirobifluorene: pure hydrocarbon small molecules as hosts for efficient green and blue PhOLEDs, S. Thiery et al., J. Mater. Chem. C, 2, 4156-4166 (2014); DOI: 10.1039/C4TC00171K.
Synthesis of 9,9'-Spirobifluorene-Based Conjugated Microporous Polymers by FeCl3-mediated Polymerization, A. Modak et al., Polym. Chem., 7, 1290-1296 (2016); 10.1039/C5PY01900A.
Highly efficient and stable organic light-emitting diode using 4,4′-bis(N-carbazolyl)-9,9′-spirobifluorene as a thermally stable host material, T. Tsuzuki et al., Appl. Phys. Lett., 94, 033302 (2009); DOI: 10.1063/1.3073709.