Issue 20, 2018

Effects of cucurbit[n]uril (n = 7, 8, 10) hosts on the formation and stabilization of a naphthalenediimide (NDI) radical anion

Abstract

Most 1,4,5,8-naphthalenediimide (NDI) derivatives, especially those with mild π-acidity cannot achieve photoinduced electron-transfer (PET). Here we report our investigations on the binding interactions of a NDI diammonium dichloride salt (NDI·Cl2) with cucurbit[n]uril (CB[n], n = 8, 10) and the formation process of a NDI radical anion upon photoexcitation of the NDI derivative in the presence of CB[n] (n = 8, 10). As a comparison, the influence of CB[7] on the PET process was also evaluated. The results show that the NDI core can be partially or fully encapsulated in CB[8] or CB[10] to form inclusion complexes at molar ratios of 1 : 1 (CB[8]·NDI2+) or 1 : 2 (CB[10]·2NDI2+). In the presence of the host, quick formation of the NDI radical anion was observed with respect to no radical anion formation without the host. According to the spectral results, interesting CB[8]-promoted charge-transfer interactions between the NDI radical anion and NDI2+ are assumed during UV irradiation. Moreover, from the UV/Vis and EPR spectra, the observation of intense signals of the NDI radical anion in the presence of CB[10], could presumably be related to a much better stabilized NDI radical anion encapsulated in CB[10].

Graphical abstract: Effects of cucurbit[n]uril (n = 7, 8, 10) hosts on the formation and stabilization of a naphthalenediimide (NDI) radical anion

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2018
Accepted
02 May 2018
First published
02 May 2018

Org. Biomol. Chem., 2018,16, 3809-3815

Effects of cucurbit[n]uril (n = 7, 8, 10) hosts on the formation and stabilization of a naphthalenediimide (NDI) radical anion

X. Zhao, F. Liu, Z. Zhao, H. Karoui, D. Bardelang, O. Ouari and S. Liu, Org. Biomol. Chem., 2018, 16, 3809 DOI: 10.1039/C8OB00664D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements