Synthesis, Aggregation Induced Emission and Mechanochromic Luminescence of New β-Diketone Derivatives Bearing Tetraphenylene Moieties

Haijie Shi, Rui Liu, Senqiang Zhu, Qiqi Gong, Hong Shi, Xiaolin Zhu, Hongjun Zhu

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A series of β-diketone derivatives bearing tetraphenylene (TPE) moieties were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. All compounds exhibit broad absorption bands between 300 and 450 nm, which are assigned to the 1π-π* transition of the conjugated system mixed intramolecular charge-transfer (ICT) transitions. Meanwhile, the emission of these compounds in solution at room temperature (λem = 458 ~ 509 nm) can be attributed to the 1π,π*/1ICT state. Introduction of freely rotatable TPE to conventional β-diketone luminophors quenches their light emissions in the solutions, but endows these molecules with aggregation-induced emission (AIE) characteristics in the condensed phase due to the restriction of intramolecular rotation. The spectroscopic studies and theoretical calculations indicate that the photophysical properties of these β-diketone derivatives can be tuned by the appended substituents, which would be useful for rational design of AIE compounds with high solid state luminescence performance. Furthermore, these AIE-active compounds exhibited distinct piezofluorochromic properties and switched reversibly upon grinding-fuming. Their photophysical properties have been investigated with the aim to provide a basis for elucidating the structure-property correlations and developing new multi-stimuli responsive luminescent materials.

Original languageEnglish (US)
Pages (from-to)2005-2013
Number of pages9
JournalJournal of Fluorescence
Volume26
Issue number6
DOIs
StatePublished - Nov 1 2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Clinical Psychology
  • Social Sciences (miscellaneous)
  • Sociology and Political Science
  • Spectroscopy
  • Clinical Biochemistry
  • Law

Keywords

  • Aggregation induced emission
  • Light-emitting materials
  • Mechanochromic luminescence
  • Optical property
  • Synthesis
  • β-diketone

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