title: Effect of AIE substituents on the fluorescence of tetraphenylethene-containing BODIPY derivatives.
abstract: A series of BODIPY derivatives with tetraphenylethene (TPE) moieties were designed and synthesized. The effect of positions and numbers of substitution groups on the fluorescence of the BODIPYs was investigated. Theoretical calculation and single crystal structures proved that the TPE substitution groups on the 8-position of BODIPY contributed little to the conjugation, but benefited the aggregated state emission. On the other hand, the substitutions on the 3- or 5-position of BODIPY through vinyl bridges increased the conjugation length, and generated big coplanar π-conjugated structures with poor aggregated state emission. The compound with bright aggregated state emission has been further fabricated into biocompatible fluorescent nanoparticles and used as effective fluorescent contrast agents for intracellular imaging.
authors.forename: Cesar F Azael
authors.initials: CF
authors.lastname: Gomez-Duran
authors.affiliation: ∥Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China.
authors.forename: Rongrong
authors.initials: R
authors.lastname: Hu
authors.affiliation: §Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, 117585, Singapore.
authors.forename: Guangxue
authors.initials: G
authors.lastname: Feng
authors.affiliation: ∥Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China.
authors.forename: Tingzhong
authors.initials: T
authors.lastname: Li
authors.affiliation: ∥Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China.
authors.forename: Fan
authors.initials: F
authors.lastname: Bu
authors.forename: Mathieu
authors.initials: M
authors.lastname: Arseneault
authors.affiliation: §Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, 117585, Singapore.
authors.forename: Bin
authors.initials: B
authors.lastname: Liu
authors.affiliation: ‡Departamento de Química, Universidad de Guanajuato, Col. Noria Alta S/N, Guanajuato, Guanajuato 36050, Mexico.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Peña-Cabrera
authors.affiliation: ∥Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology (SCUT), Guangzhou 510640, China.|⊥HKUST-Shenzhen Research Institute, No. 9 Yuexing First RD, South Area, Hi-Tech Park, Nanshan, Shenzhen 518057, China.
authors.forename: Ben Zhong
authors.initials: BZ
authors.lastname: Tang
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005030:Ethylenes; D005456:Fluorescent Dyes
keywords: BODIPY; aggregation-induced emission; cellular imaging; substitution effect; tetraphenylethene