Tetraphenylethene-based star shaped porphyrins: Synthesis, self-assembly, and optical and photophysical study

Anushri Rananaware, Rajesh S. Bhosale, Kei Ohkubo, Hemlata Patil, Lathe A. Jones, Sam L. Jackson, Shunichi Fukuzumi, Sheshanath V. Bhosale, Sidhanath V. Bhosale

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

Supramolecular self-assembly and self-organization are simple and convenient ways to design and create controlled assemblies with organic molecules, and they have provoked great interest due to their potential applications in various fields, such as electronics, photonics, and light-energy conversion. Herein, we describe the synthesis of two π-conjugated porphyrin molecules bearing tetraphenylethene moieties with high fluorescence quantum yield. Photophysical and electrochemical studies were conducted to understand the physical and redox properties of these new materials, respectively. Furthermore, these derivatives were used to investigate self-assembly via the solvophobic effect. The self-assembled aggregation was performed in nonpolar and polar organic solvents and forms nanospheres and ring-like nanostructures, respectively. The solution based aggregation was studied by means of UV-vis absorption, emission, XRD, and DLS analyses. Self-assembled ring-shape structures were visualized by SEM and TEM imaging. This ring-shape morphology of nanosized macromolecules might be a good candidate for the creation of artificial light-harvesting nanodevices.

Original languageEnglish
Pages (from-to)3832-3840
Number of pages9
JournalJournal of Organic Chemistry
Volume80
Issue number8
DOIs
StatePublished - 17 Apr 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

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