journal article·2015-07-22

Effect of AIE Substituents on the Fluorescence of Tetraphenylethene-Containing BODIPY Derivatives

Cesar F. Azael Gomez-Duran, Rongrong Hu, Guangxue Feng, Tingzhong Li, Fan Bu, Mathieu Arseneault, Bin Liu, Eduardo Peña-Cabrera, Ben Zhong Tang

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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.
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Research context

OpenAlex topics: Luminescence and Fluorescent Materials · Nanoplatforms for cancer theranostics · Molecular Sensors and Ion Detection

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, Institute for Advanced Study, Institute of Molecular Functional Materials, Division of Biomedical Engineering, Division of Life Science, and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science & Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong

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

Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, 117585, Singapore

Departamento de Química, Universidad de Guanajuato, Col. Noria Alta S/N, Guanajuato, Guanajuato 36050, Mexico

HKUST-Shenzhen Research Institute, No. 9 Yuexing First RD, South Area, Hi-Tech Park, Nanshan, Shenzhen 518057, China

Funding

Ministry Of Defence- Singapore · Guangdong Innovative Research Team Program · Innovation and Technology Commission, Government of the Hong Kong Special Administrative Region · National Research Foundation-Prime Minister's office, Republic of Singapore · Research Grants Council, University Grants Committee, Hong Kong · University Grants Committee · National University of Singapore · Consejo Nacional de Ciencia y Tecnología · Ministry of Science and Technology of the People's Republic of China · Economic Development Board - Singapore

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