Synthesis and photophysical properties of axially substituted silicon (IV) tetrapyrazinoporphyrazines

• Published in: Inorganic chemistry communications 2015-12, Vol.62, p.64-66
• Main Authors: Park, Jong min, Jung, Chang Young, Song, Cheol Jun, Jaung, Jae Yun
• Format: Article
• Language: English
• Subjects: Aggregation; Camphorquinone; Fluorescence quantum yield; Fluorescence quenching; Silicon tetrapyrazinoporphyrazine
• ISSN: 1387-7003; 1879-0259
• DOI: 10.1016/j.inoche.2015.10.015

We successfully synthesized non-aggregated silicon (IV) tetrapyrazinoporphyrazines (SiPz) bearing bornane groups at their peripheral positions. The UV–vis spectra of the SiPz complexes maintained a strong and sharp Q-band, which is an archetypal characteristic of non-aggregated phthalocyanines, in various organic solvents. In addition, the extreme red emission of SiPz complexes 4a–4c under visible light in a neutral solution condition was observed. However, the SiPz complex (4d) with axial aniline groups had very low fluorescence quantum yields due to the quenching ability of the aniline group. Axially substituted silicon (IV) tetrapyrazinoporphyrazines bearing bornane groups at their peripheral positions have been reported. Detailed synthesis and optical properties have been described. The spectral properties were influenced by the type of axial substituents. [Display omitted] •We design and synthesize silicon (IV) tetrapyrazinoporphyrazines (SiPz) derived from 5,9,9-trimethyl-5,6,7,8-tetrahydro-1,8-methanoquinoxaline-2,3-dicarbonitrile.•Various substituents were introduced at the axial positions of the tetrapyrazinoporphyrazine to inhibit aggregation and fluorescence quenching as well as to improve the solubility in organic solvents.•SiPz axially substituted with aniline groups quenched fluorescence of compound caused by photo induced transfer effect.