Synthesis of polypeptides with asymmetric perylene diimide side chains
Perylenetetracarboxylic diimides (PDI) and their derivatives have been paid more attention due to their special photophysical and electrochemical properties. The modification on molecular structure of PDI aimed at changing the photophysical properties is one of an important means to obtain functiona...
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Hebei University of Science and Technology
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doaj-dcc2c3989d8840078f69c54eb317e5fa2020-11-24T23:30:06ZzhoHebei University of Science and TechnologyJournal of Hebei University of Science and Technology1008-15422018-04-0139214915310.7535/hbkd.2018yx02008b201802008Synthesis of polypeptides with asymmetric perylene diimide side chainsXiaoli ZHEN0Xiaohao LI1Yang ZHANG2School of Science, Hebei University of Science and Technology, Shijiazhuang, Hebei 050018, ChinaSchool of Science, Hebei University of Science and Technology, Shijiazhuang, Hebei 050018, ChinaSchool of Science, Hebei University of Science and Technology, Shijiazhuang, Hebei 050018, ChinaPerylenetetracarboxylic diimides (PDI) and their derivatives have been paid more attention due to their special photophysical and electrochemical properties. The modification on molecular structure of PDI aimed at changing the photophysical properties is one of an important means to obtain functional materials of PDI. An asymmetric PDI containing polypeptide chain at one imide nitrogen is synthesized by stepwise aminolysis reaction of 3,4,9,10-perylenetetracarboxylic dianhydride. The influence of reactions on yield is then inquired. The optimal reaction condition are determined as follows: molar ratio of PDI to cyclohexylamine, 1∶6; the solvent volume ratio of ethanol to water, 4∶1; reaction temprature and time, 70 ℃ and 6 h, the intermediate N-cyclohexyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide. In the presence of the catalyst DMAP, this intermediate undergoing aminolysis reaction with L-Ala-D-Leu-(N-Me)-Ala-D-Leu-Ally affords polypeptides with asymmetric PDI in imidazole for 4 h at 120 ℃, and the tatal yield is above 32.6%. The product structure is characterized by ESI-MS and 1H-NHR. The process is simple and mild conditions, which provides a convenient synthetic route for the preparation of asymmetric PDI compounds.http://xuebao.hebust.edu.cn/hbkjdx/ch/reader/create_pdf.aspx?file_no=b201802008&flag=1&journal_organic synthesis chemistryperylene anhydrideperylene diimideasymmetricchain tetrapeptidesynthesis |
collection |
DOAJ |
language |
zho |
format |
Article |
sources |
DOAJ |
author |
Xiaoli ZHEN Xiaohao LI Yang ZHANG |
spellingShingle |
Xiaoli ZHEN Xiaohao LI Yang ZHANG Synthesis of polypeptides with asymmetric perylene diimide side chains Journal of Hebei University of Science and Technology organic synthesis chemistry perylene anhydride perylene diimide asymmetric chain tetrapeptide synthesis |
author_facet |
Xiaoli ZHEN Xiaohao LI Yang ZHANG |
author_sort |
Xiaoli ZHEN |
title |
Synthesis of polypeptides with asymmetric perylene diimide side chains |
title_short |
Synthesis of polypeptides with asymmetric perylene diimide side chains |
title_full |
Synthesis of polypeptides with asymmetric perylene diimide side chains |
title_fullStr |
Synthesis of polypeptides with asymmetric perylene diimide side chains |
title_full_unstemmed |
Synthesis of polypeptides with asymmetric perylene diimide side chains |
title_sort |
synthesis of polypeptides with asymmetric perylene diimide side chains |
publisher |
Hebei University of Science and Technology |
series |
Journal of Hebei University of Science and Technology |
issn |
1008-1542 |
publishDate |
2018-04-01 |
description |
Perylenetetracarboxylic diimides (PDI) and their derivatives have been paid more attention due to their special photophysical and electrochemical properties. The modification on molecular structure of PDI aimed at changing the photophysical properties is one of an important means to obtain functional materials of PDI. An asymmetric PDI containing polypeptide chain at one imide nitrogen is synthesized by stepwise aminolysis reaction of 3,4,9,10-perylenetetracarboxylic dianhydride. The influence of reactions on yield is then inquired. The optimal reaction condition are determined as follows: molar ratio of PDI to cyclohexylamine, 1∶6; the solvent volume ratio of ethanol to water, 4∶1; reaction temprature and time, 70 ℃ and 6 h, the intermediate N-cyclohexyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide. In the presence of the catalyst DMAP, this intermediate undergoing aminolysis reaction with L-Ala-D-Leu-(N-Me)-Ala-D-Leu-Ally affords polypeptides with asymmetric PDI in imidazole for 4 h at 120 ℃, and the tatal yield is above 32.6%. The product structure is characterized by ESI-MS and 1H-NHR. The process is simple and mild conditions, which provides a convenient synthetic route for the preparation of asymmetric PDI compounds. |
topic |
organic synthesis chemistry perylene anhydride perylene diimide asymmetric chain tetrapeptide synthesis |
url |
http://xuebao.hebust.edu.cn/hbkjdx/ch/reader/create_pdf.aspx?file_no=b201802008&flag=1&journal_ |
work_keys_str_mv |
AT xiaolizhen synthesisofpolypeptideswithasymmetricperylenediimidesidechains AT xiaohaoli synthesisofpolypeptideswithasymmetricperylenediimidesidechains AT yangzhang synthesisofpolypeptideswithasymmetricperylenediimidesidechains |
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1725542862250049536 |