Cat. No JK1784534_1_G
J&K Chemical

Product Information

Product Name
2-Bromospirfluorene-9,9'-xanthene, 95%
Brand Name
J&K
Product Number
1784534
CAS
899422-06-1
Molecular Formula
C25H15BrO
Molecular Weight
411.29
SDS Document
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
11546047
IUPAC Name
2-bromospirofluorene-9,9'-xanthene
InChI Key
MNBDZJINQUZDFP-UHFFFAOYSA-N
SMILES
C1=CC=C2C(=C1)C3=C(C24C5=CC=CC=C5OC6=CC=CC=C46)C=C(C=C3)Br

Safety Information

Precautionary Statement
p262

Description

Description and Applications

Spiro aromatic compounds are an important class of building blocks for organic semiconductors. Their unique orthogonal spiro-conjugated architecture, rigid three-dimensional configuration, and intrinsic steric hindrance effectively improve the optoelectronic properties, thermal stability, and morphological stability of organic electronic materials.

Among them, Spirofluorene-9,9'-xanthene (SFX) has emerged as a next-generation spiro scaffold owing to its efficient one-pot synthetic methodology, which significantly simplifies the preparation process compared with conventional spirobifluorene derivatives while reducing production cost. As a versatile molecular platform, SFX-based intermediates have attracted extensive attention in the development of OLED materials, organic lasers, organic field-effect transistors (OFETs), perovskite solar cells (PSCs), and other advanced optoelectronic devices.

2,7-Dibromospirofluorene-9,9'-xanthene features two reactive bromine atoms that enable further functionalization through Suzuki–Miyaura, Stille, Negishi, Kumada, and other palladium-catalyzed cross-coupling reactions, making it an excellent intermediate for constructing high-performance π-conjugated materials.

Features & Benefits

  • Improves the quantum efficiency of OLED and other optoelectronic devices
  • Enhances thermal, morphological, and photochemical stability of organic semiconductor materials
  • Rigid three-dimensional spiro framework suppresses intermolecular aggregation
  • Highly versatile intermediate for molecular design and structural modification
  • Excellent precursor for functional organic electronic materials
  • Cost-effective and scalable synthetic platform with promising industrial potential

References

  1. Ling-Hai Xie, Feng Liu, Chao Tang, Xiao-Ya Hou, Yu-Ran Hua, Qu-Li Fan, Wei Huang. Org. Lett. 2006, 8, 2787-2790.
  2. Jie Zhao, Guo-Hua Xie, Cheng-Rong Yin, Ling-Hai Xie, Chun-Miao Han, Run-Feng Chen, Hui Xu, Ming-Dong Yi, Zhao-Peng Deng, Shu-Fen Chen, Yi Zhao, Shi-Yong Liu, Wei Huang. Chem. Mate. 2011, 23, 5331-5339.
  3. Jing Li, Dongxue Ding, Youtian Tao, Ying Wei, Runfeng Chen, Linghai Xie, Wei Huang, Hui Xu. Adv. Mater. 2016, 28, 3122.
  4. Mingli Sun, Ruochen Xu, Linghai Xie, Ying Wei, Wei Huang. Chin. J. Chem. 2015, 33, 815-827.
  5. Zong-Qiong Lin, Jin Liang, Peng-Ju Sun, Feng Liu, Yee-Yan Tay, Ming-Dong Yi, Kun Peng, Xian-Hai Xia, Ling-Hai Xie, Xin-Hui Zhou, Jian-Feng Zhao, and Wei Huang. Adv. Mater. 2013, 25, 3664.

References Data Source From Pubchem

An Efficient One-Pot Synthesis of Spiro[fluorene-9,9′-xanthene]

Publication Name: Synfacts
Publication Date: 2006-09
DOI: 10.1055/s-2006-942036

2-Bromospir[fluorene-9,9'-xanthene], 95%

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