ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle

Le Fang, Wei-Tao Gong, Manivannan Kalavathi Dhinakaran, Li Shang, and Gui-Ling Ning

^aState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China

E-mail: wtgong@dlut.edu.cn

Abstract: Anovel Hg²⁺ ion induced reversible ring contraction was achieved employing the intramolecular reaction of isobutylene with an aromatic hydroxyl group of cyclophane; reversibility of the reaction was facilitated by excess addition of NaBH₄ which also resulted in complexation. The ring contraction and expansion was monitored by UV-VIS absorption, and by fluorescence and ¹HNMR spectra. Switchable fluorescence behavior (on–off–on) was observed when the ring-size was tuned from a 19-membered ring to an 18-membered and vice versa. This fine tuning has the potential to be applied in the construction of new supramolecular devices.

Keywords: cyclophane – reversible reaction – ring-size of macrocycle – supramolecular devices

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0241

Chemical Papers 70 (5) 663–666 (2016)