Issue 23, 2013
From the journal:

Chemical Communications

Unusual conformational preference of an aromatic secondary urea: solvent-dependent open-closed conformational switching of N,N′-bis(porphyrinyl)urea†

Mio Matsumura,a   Aya Tanatani,*a   Isao Azumaya,b   Hyuma Masu,c   Daisuke Hashizume,d   Hiroyuki Kagechika,e   Atsuya Muranaka*d  and  Masanobu Uchiyama*df  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
E-mail: tanatani.aya@ocha.ac.jp
Fax: +81-3-5978-2716

b Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan
E-mail: i-az@kph.bunri-u.ac.jp

c Chemical Analysis Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
E-mail: masu@faculty.chiba-u.jp

d Advanced Technology Support Division and Advanced Elements Chemistry Research Team, RIKEN-ASI, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
E-mail: atsuya-muranaka@riken.jp
Fax: +81-48-467-2869

e Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: kage.chem@tmd.ac.jp

f Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: uchiyama@mol.f.u-tokyo.ac.jp
Fax: +81-3-5841-0732

Abstract

N,N′-Bis(2,3,7,8,12,13,17,18-octaethylporphyrin-5-yl)urea (3) exhibits cis–trans conformational switching depending on the solvent properties, and can adopt the cofacial porphyrin dimer structure under certain conditions. The conformational preference can be switched by electrochemical stimulus.

Graphical abstract: Unusual conformational preference of an aromatic secondary urea: solvent-dependent open-closed conformational switching of N,N′-bis(porphyrinyl)urea

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Article information

DOI
https://doi.org/10.1039/C2CC37583D
Article type
Communication
Submitted
17 Oct 2012
Accepted
19 Nov 2012
First published
19 Nov 2012

Chem. Commun., 2013,49, 2290-2292

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Unusual conformational preference of an aromatic secondary urea: solvent-dependent open-closed conformational switching of N,N′-bis(porphyrinyl)urea

M. Matsumura, A. Tanatani, I. Azumaya, H. Masu, D. Hashizume, H. Kagechika, A. Muranaka and M. Uchiyama, Chem. Commun., 2013, 49, 2290 DOI: 10.1039/C2CC37583D

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