Jump to main content
Jump to site search


Design of Rigid Cyclic Tripyrrins: The Importance of Intermolecular Interactions on Aggregation and Luminescence

Abstract

We designed a cyclic tripyrrin “locked” by a bridging benzene-1,4-diol moiety which is perpendicular to tripyrrin plane. The cyclic structures promote the scaffold rigidity and enhances the fluorescence. While the halogen-substitution of bridging moiety was found to slightly affect the fluorescence of 1-3 in solution, such substitution significantly affects the aggregation behaviours and solid emission. 1 and 2 exhibit typical J-aggregate emission but 3 does not. Analysis of crystal packing combining with reduce density gradient (RDG) analysis suggest that the bridging moieties of 1-3 play an important role to induce the different crystal packing by tuning intermolecular interaction in solid state. Energy decomposition analysis using symmetry adapted perturbation theory (SAPT) revealed that such weak intermolecular interactions are mainly consist of halogen bond and π-π interactions.

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Mar 2018, accepted on 10 Apr 2018 and first published on 11 Apr 2018


Article type: Research Article
DOI: 10.1039/C8QO00313K
Citation: Org. Chem. Front., 2018, Accepted Manuscript
  •   Request permissions

    Design of Rigid Cyclic Tripyrrins: The Importance of Intermolecular Interactions on Aggregation and Luminescence

    J. Wang, Y. Yao, Y. Ning, Y. Meng, C. Hou, J. Zhang and J. Zhang, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO00313K

Search articles by author

Spotlight

Advertisements