Highly fluorescent intramolecular dimmers of two pyrenyl-substituted fluorenes bridged by 1,6-hexanyl: synthesis, spectroscopic, and self-organized properties

• Published in: Tetrahedron letters Vol. 51; no. 9; pp. 1317 - 1321
• Main Authors: He, Chao, He, Qingguo, Chen, Qing, Shi, Liqi, Cao, Huimin, Cheng, Jiangong, Deng, Changmin, Lin, Tong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.03.2010; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; DERIVATIVES; ELECTROLUMINESCENCE; CARBAZOLE
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2009.12.136

Two intramolecular fluorene dimmers (structure as illustrated) have been synthesized, and they both have shown very high fluorescent efficiency, can self-organize into spherical particles from solutions due to evaporation of the solvent. Two intramolecular dimmers of 4-, 8-pyrenyl-substituted fluorenes bridged by 1,6-hexanyl unit have been synthesized. They showed very strong fluorescent emission with the emission peak at around 450 nm and fluorescence efficiency as high as ∼0.9. The absorption spectra also had high extinction coefficients. The cyclic voltammetric curves showed that they can be used as electron-donating materials. The DSC results suggested the dimmers have higher glass transition temperature. It was also found that these novel dimmers can self-organize into spherical particles from the solutions due to evaporation of the solvent.