- A novel NIR violanthrone derivative with high electron-deficiency: Effect of fluorescence on dicyanomethylene substitution
-
Near infrared (NIR) dyes attracted increasing interests in widely potential applications, such as fluorescent probe and living organism imaging, due to their low background signals from biomolecules, low light scattering and deep penetration, and low-cost excitation light sources. A novel NIR violanthrone derivative (VA-CN) with dicyanomethylene substitution was synthesized and fully characterized by 1H NMR, 13C NMR, HRMS, and IR spectrometry. It is demonstrated that the original planar conformation of violanthrone ring (the nine fused benzene rings) becomes twisted and unsymmetrical upon the incorporation of two strong electron-withdrawing dicyanomethylene units. Photophysical, electrochemical performances as well as distinct solvatochromic effects were studied in detail. Considering the low reduction potential (-0. 56 V vs NHE), VA-CN could be considered as a good electron acceptor due to the strong electron deficiency resulted from dicyanomethylene group. A distinct increase in fluorescence was observed with 30-fold enhancement upon the addition of n-butyl amine. The reversible fluorescence "off-on" shows that VA-CN might be served as a promising fluorescent sensor for electron-rich amines.
- Liu, Bo,Fan, Duo,Zhang, Qiong,Chen, Yu,Zhu, Weihong
-
-
Read Online
- A 16, 17-double-alkoxy Anthracyclinone purple method for preparing derivatives of
-
The invention discloses a method for preparing 16,17-dialkoxyviolanthrone derivatives. A readily available 16,17-dimethoxyviolanthrone dye is used as an initial raw material, a 16,17-dihydroxyviolanthrone intermediate is prepared through demethylation, and the corresponding 16,17-dialkoxyviolanthrone derivatives are synthesized through Williamson ether synthesis reaction. The method has the characteristics of short whole reaction route, high yield, mild reaction conditions and low cost.
- -
-
-
- Effect of substituents on the aggregate structure and photovoltaic property of violanthrone derivatives
-
In this paper, three violanthrone derivatives with different substituents, 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (3), 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (4), 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (5), are synthesized. It is found that the substituent has a great effect on the aggregate structures of violanthrone derivatives: the shorter the side chain is, the stronger the intermolecular π-π actions in the solid state is. Because all compounds are p-type semiconductive materials with the relatively low-lying highest occupied molecular orbital (HOMO) energy levels (~-5.1 eV) and low band gaps (~1.8 eV), their photovoltaic properties are evaluated when the blends of violanthrone derivatives and [6,6]-phenyl-C 61-butyric acid methyl ester (PCBM) (1:1, w/w) are used as the active layers of organic solar cells. Among three violanthrone derivatives, compound 5 exhibits the best photovoltaic performance with the power conversion efficiency (PCE) of 0.54% since the aggregate structure of compound 5 is in favor of charge transport.
- Shi, Minmin,Hao, Feng,Zuo, Lijian,Chen, Yi,Nan, Yaxiong,Chen, Hongzheng
-
scheme or table
p. 377 - 383
(2012/09/11)
-