Synthesis of Regioisomerically Pure 1,7-Dibromoperylene-3,4,9,10-tetracarboxylic Acid Derivatives
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- 作者：Sanchita Sengupta ; Rajeev K. Dubey ; Rob W. M. Hoek ; Sjoerd P. P. van Eeden ; D. Deniz Gunba艧 ; Ferdinand C. Grozema ; Ernst J. R. Sudh枚lter ; Wolter F. Jager
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：July 18, 2014
- 年：2014
- 卷：79
- 期：14
- 页码：6655-6662
- 全文大小：399K
- ISSN：1520-6904
文摘
The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the 鈥減eri鈥?and the 鈥渂ay鈥?positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.