159-62-6

Basic information

• Product Name: Spiro[fluorene-9,9'-xanthene]
• Synonyms: Spiro[fluorene-9,9'-xanthene];SFX
• CAS NO: 159-62-6
• Molecular Formula: C₂₅H₁₆O
• Molecular Weight: 332.39394
• Mol File: 159-62-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 212-213 °C
• Boiling Point: 472.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Spiro[fluorene-9,9'-xanthene](CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[fluorene-9,9'-xanthene](159-62-6)
• EPA Substance Registry System: Spiro[fluorene-9,9'-xanthene](159-62-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 159-62-6(Hazardous Substances Data)

Usage

Description

Spiro[fluorene-9,9'-xanthene] is a complex spiro compound with a unique molecular structure, derived from fluorene and xanthene, two aromatic hydrocarbons. It features two fused ring systems sharing a single atom, and is known for its high thermal stability and electron transporting capabilities, making it a significant compound in the realm of organic chemistry.

Uses

Used in Optoelectronic Industry:
Spiro[fluorene-9,9'-xanthene] is used as a key component in the development of organic light emitting diodes (OLEDs) for its high thermal stability and electron transporting properties, which are crucial for the performance and longevity of these devices.
Used in Material Science:
In the field of material science, Spiro[fluorene-9,9'-xanthene] is utilized for its unique properties, contributing to the advancement of new materials with potential applications in various technological areas, including but not limited to optoelectronics.

Upstream product

• 859933-74-7 9-hydroxy-9-(2-phenoxy-phenyl)-fluorene 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 92-83-1 xanthene 
• 1016-05-3 dibenzothiophene sulfone 
• 108-95-2 phenol 
• 486-25-9 9-fluorenone 

Relevant articles and documents

Low-cost synthesis of heterocyclic spiro-type hole transporting materials for perovskite solar cell applications

Four heterocyclic spiro-type hole transporting materials (HTMs) carrying a spiro[fluorene-9,9′-xanthene] (SFX) (SFX-TPAM and SFX-TPA) or spiro[fluorene-9,9′-thioxanthene] (SFT) unit (SFT-TPAM and SFT-TPA) were synthesized through a low-cost facile route with high yields for perovskite solar cell (PSC) applications. In terms of absorption, these four compounds in the film state are all transparent at wavelengths longer than 430 nm, which is beneficial for allowing visible light to reach the perovskite active layer without being absorbed by the hole transporting layer (HTL). The photovoltaic performance of the inverted PSCs based on these small molecular HTMs with the device architecture of glass/ITO/HTL/CH3NH3PbI3/C60/BCP/Ag was tested. Only SFX-TPAM had its highest occupied molecular orbital (HOMO) level matched with the valence band of CH3NH3PbI3. The inverted PSC based on a dopant-free SFX-TPAM HTL achieves a power conversion efficiency of 10.23% under the illumination of standard one sun lighting, which is better than that (8.17%) of the cell based on dopant-free spiro-OMeTAD. The better photovoltaic performance of SFX-TPAM compared to spiro-OMeTAD may be due to the MAPbI3 film deposited on it having better quality. These results indicate that the facilely synthesized, low-cost SFX based small molecules can be used as the HTMs for PSCs.

Unexpected one-pot method to synthesize spiro[fluorene-9,9′-xanthene] building blocks for blue-light-emitting materials

An unexpected one-pot synthetic approach toward spiro[fluorene-9,9′- xanthene] (SFX) under excessive MeSO3H conditions has been developed. The key step involves a thermodynamically controlled cyclization reaction. Blue-light-emitting materials based on SFX building blocks that exhibit high thermal stability have also been synthesized.

Synthesis of spirocyclic diarylfluorenes by one-pot twofold SNAr reactions of diaryl sulfones with diarylmethanes

Treatment of dibenzothiophene dioxides with cyclic diarylmethanes in the presence of KN(SiMe3)2 results in the formation of fluorene-based spirocyclic tetraarylmethanes in a single operation. The transformation would proceed via an intermolecular SNAr reaction of the dioxides with cyclic diarylmethylpotassium followed by intramolecular SNAr cyclization. This straightforward strategy provides a wide range of spirocyclic diarylfluorenes including unusual ones that are otherwise difficult to synthesize.