An efficient synthesis of novel spiro[[8 H]indeno[2,1- b]-thiophene-8,9′-fluorene] building block for blue light-emitting materials

• Published in: Tetrahedron letters Vol. 47; no. 36; pp. 6421 - 6424
• Main Authors: Xie, Ling-Hai, Fu, Ting, Hou, Xiao-Ya, Tang, Chao, Hua, Yu-Ran, Wang, Rui-Jie, Fan, Qu-Li, Peng, Bo, Wei, Wei, Huang, Wei
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.09.2006; Elsevier
• Subjects: BF 3·Et 2O; Blue light-emitting materials; Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Spiro compounds; Spiroindenothiophenefluorene; Spiroindenothiophenefluorene; Spiro compounds; Blue light-emitting materials; BF 3·Et 2O; HOLE TRANSPORT; CONJUGATED POLYMERS; STABILITY; blue light-emitting materials; BF3 center dot Et2O; DIODES; spiro compounds; spiroindenothiophenefluorene
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2006.06.143

We have developed efficient synthetic routes to obtain a novel building block spiro[[8 H]indeno[2,1- b]thiophene-8,9′-fluorene] (SITF) and constructed a blue light-emitting material 2′,7′-bis-(9,9′-spirobifluoren-2-yl)spiro[[8 H]indeno[2,1- b]thiophene-8,9′-fluorene] (BSBF–SITF). Light-emitting materials based on SITF with unique regioselective feature will be promising for constructing complicated optoelectrical systems. We have developed efficient synthetic routes to obtain a novel building block spiro[[8 H]indeno[2,1- b]thiophene-8,9′-fluorene] (SITF), a monothiophene-containing spirobifluorene analogue, and constructed blue light-emitting materials, including 2′,7′-bis([1,1′-biphenyl]-4-yl)-spiro[indeno[2,1- b]thiophene-8,9′-fluorene] (BBP–SITF) and 2′,7′-bis(9,9′-spirobifluoren-2-yl)spiro[[8 H]indeno[2,1- b]-thiophene-8,9′-fluorene] (BSBF–SITF). BSBF–SITF has shown to be a stable blue light-emitting material with high PL quantum efficiency (89%) and unique regioselective feature at the C2 of thiophene, which indicate that BSBF–SITF will be useful for constructing complicated optoelectronic systems.