Citation: Jiang Nan, Wang Yijia, Qin Anjun, Sun JingZhi, Tang BenZhong. Effective enhancement of the emission efficiency of tetraphenylporphyrin in solid state by tetraphenylethene modification[J]. Chinese Chemical Letters, ;2019, 30(1): 143-148. doi: 10.1016/j.cclet.2018.10.020 shu

Effective enhancement of the emission efficiency of tetraphenylporphyrin in solid state by tetraphenylethene modification

Jiang Nan ^a ,
Wang Yijia ^a ,
Qin Anjun ^b ,
Sun JingZhi ^a,, ,
Tang BenZhong ^a,b,c,,

a.
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
b.
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510641, China
c.
Department of Chemistry, Institute for Advanced Study, Institute of Molecular Functional Materials, and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science & Technology, Hong Kong, China

Corresponding author: Sun JingZhi, sunjz@zju.edu.cn Tang BenZhong, tangbenz@sut.hk
Received Date: 4 July 2018
Revised Date: 24 August 2018
Accepted Date: 18 October 2018
Available Online: 28 January 2018

Figures(6)

Tetraphenylporphyrin (TPP) is a typical red-emitting luminogen showing evident aggregation caused quenching (ACQ) effect. To enhance its emission efficiency in solid state, four tetraphenylethene (TPE) units were attached to the four meso-positions of TPP core via ester group through a facile and efficient route. The derived compound (4(TPE COO)-TPP) emits red fluorescence (peak at 655 nm) with a good quantum efficiency (Φ) of 7.5%, which is much higher than that of TPP (Φ~0.1%). In molecular aggregate formed in tetrahydrofuran (THF) and water mixtures, 4(TPE COO)-TPP has a relative high Φ of 12%. The evidently subdued ACQ behavior can be ascribed to the propeller shape and bulky size of the TPE units, which prevent the close packing and strong π-π interaction of TPP cores. The loose molecular packing and weak interchromophore interactions were validated by different characterization methods including UV-visible absorption, steady state and transient fluorescence spectroscope, X-ray diffraction and scanning electronic microscope observations. It is noted that 4(TPE COO)-TPP has an emission efficiency of 14.4% in dilute THF solution. This is due to the conjugation break between the TPP and TPE moieties, the rotational and vibrational motions of the phenyl groups cannot quench the fluorescence of 4(TPE COO)-TPP.
- Aggregation-induced emission,
- Tetraphenylethene,
- Porphyrin,
- Red emission,
- Molecular packing
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