Synthesis, Structures, and Photophysical Properties of Alternating Donor-Acceptor Cycloparaphenylenes

Shuhei Nishigaki; Miho Fukui; Haruki Sugiyama; Hidehiro Uekusa; Susumu Kawauchi; Yu Shibata; Ken Tanaka

doi:10.1002/chem.201701547

Synthesis, Structures, and Photophysical Properties of Alternating Donor-Acceptor Cycloparaphenylenes

Chemistry. 2017 May 29;23(30):7227-7231. doi: 10.1002/chem.201701547. Epub 2017 May 2.

Authors

Shuhei Nishigaki¹, Miho Fukui^{1

2}, Haruki Sugiyama³, Hidehiro Uekusa³, Susumu Kawauchi¹, Yu Shibata¹, Ken Tanaka^{1

2}

Affiliations

¹ Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
² Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
³ Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

PMID: 28402001
DOI: 10.1002/chem.201701547

Abstract

The synthesis of alternating donor-acceptor [12] and [16]cycloparaphenylenes (CPPs) has been achieved by the rhodium-catalyzed intermolecular cross-cyclotrimerization followed by imidation and/or aromatization. These alternating donor-acceptor CPPs showed positive solvatofluorochromic properties and smaller HOMO-LUMO gaps compared with nonfunctionalized CPPs, which was confirmed by the theoretical study.

Keywords: cycloparaphenylenes; cyclotrimerization; donor-acceptor systems; rhodium; solvatochromism.