Jump to main content
Jump to site search

Issue 15, 2015
Previous Article Next Article

The fluorescence properties and aggregation behavior of tetraphenylethene–perylenebisimide dyads

Author affiliations

Abstract

Two tetraphenylethene (TPE) modified perylenebisimides (PBIs) were synthesized through linking the TPE moieties to the PBI core at the imide positions. Theoretical calculations predict that, in both of the mono-TPE and di-TPE substituted derivatives (i.e. TPE-N-PBI and DTPE-N-PBI), the TPE and PBI units are orthogonal to each other, and thus have no electronic conjugation. Thus the two compounds are TPE–PBI dyads rather than TPE–PBI conjugates. This property is supported by absorption and emission spectral features. In solution, aggregate and solid film, the fluorescence from both TPE and PBI subunits is evidently quenched. The underlying mechanism is the photo-induced charge transfer between the electron donor TPE and electron acceptor PBI subunits. In a highly polar tetrahydrofuran–water mixture with a large fraction of water, TPE-N-PBI can form H-aggregates. In low polar hydrophobic dichloromethane–hexane mixtures, due to the bulky size and rigidity of the TPE subunit, the dyad molecules cannot take a parallel alignment to form classical J- or H-aggregates, but have to exist in a large offset angle. Consequently, X-aggregates are formed, which was confirmed by the absorption features, morphological observations and comparative investigation of the reference compound.

Graphical abstract: The fluorescence properties and aggregation behavior of tetraphenylethene–perylenebisimide dyads

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Nov 2014, accepted on 22 Feb 2015 and first published on 26 Feb 2015


Article type: Paper
DOI: 10.1039/C4TC02550D
Author version
available:
Download author version (PDF)
Citation: J. Mater. Chem. C, 2015,3, 3559-3568
  •   Request permissions

    The fluorescence properties and aggregation behavior of tetraphenylethene–perylenebisimide dyads

    Y. J. Wang, Z. Li, J. Tong, X. Y. Shen, A. Qin, J. Z. Sun and B. Z. Tang, J. Mater. Chem. C, 2015, 3, 3559
    DOI: 10.1039/C4TC02550D

Search articles by author

Spotlight

Advertisements