π-Extended "Earring" Porphyrins with Multiple Cavities and Near-Infrared Absorption

Yutao Rao; Taeyeon Kim; Kyu Hyung Park; Fulei Peng; Lei Liu; Yunmei Liu; Bin Wen; Shubin Liu; Steven Robert Kirk; Licheng Wu; Bo Chen; Ming Ma; Mingbo Zhou; Bangshao Yin; Yuexing Zhang; Dongho Kim; Jianxin Song

doi:10.1002/anie.201600955

π-Extended "Earring" Porphyrins with Multiple Cavities and Near-Infrared Absorption

Angew Chem Int Ed Engl. 2016 May 23;55(22):6438-42. doi: 10.1002/anie.201600955. Epub 2016 Apr 1.

Authors

Yutao Rao¹, Taeyeon Kim², Kyu Hyung Park², Fulei Peng¹, Lei Liu¹, Yunmei Liu¹, Bin Wen¹, Shubin Liu^{1

3}, Steven Robert Kirk¹, Licheng Wu¹, Bo Chen¹, Ming Ma¹, Mingbo Zhou¹, Bangshao Yin¹, Yuexing Zhang⁴, Dongho Kim⁵, Jianxin Song⁶

Affiliations

¹ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of Application and Assemble of Organic Functional Molecules, Hunan Normal University, Changsha, 410081, China.
² Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 03722, Korea.
³ Division of Research Computing, Information Technology Services, University of North Carolina, Chapel Hill, NC, 27599, USA.
⁴ Department of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education), 15 Yucai Road, Guilin, 541004, China.
⁵ Spectroscopy Laboratory for Functional π-Electronic Systems and Department of Chemistry, Yonsei University, Seoul, 03722, Korea. [email protected].
⁶ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of Application and Assemble of Organic Functional Molecules, Hunan Normal University, Changsha, 410081, China. [email protected].

PMID: 27038255
DOI: 10.1002/anie.201600955

Abstract

β,β-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule. The structures of the porphyrins have been elucidated by x-ray diffraction analysis, and feature curved π planes. The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features. Electrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties.

Keywords: conjugation; near-infrared absorption; nickel; palladium; porphyrinoids.

Publication types

Research Support, Non-U.S. Gov't