| Selective bromination of perylene diimides under mild conditions. | |
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MedLine Citation:
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PMID: 17604397 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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A novel method for the bromination of perylene diimides, PDI (1), under mild conditions is reported. Variation of the reaction conditions allows mono- and dibromination of PDIs to afford 2 and 3 (these can be separated through standard procedures) or exclusive dibromination to afford 3. Pure 1,7 regioisomers are obtained through repetitive crystallization. The structure of 1,7-3b was elucidated by a single-crystal X-ray analysis. The facility of the bromination reaction, which decreases in the order 1a > 1b > 1c, depends on PDI aggregation propensities. Monobrominated PDIs were utilized for the syntheses of novel unsymmetrical piperidinyl (4a and 4b) and trimethylsilylethynyl derivatives (5a and 5b). Computational studies (DFT) on imide substituent rotation in PDIs reveal that in the case of bulky groups there is a restricted rotation leading to isomers, in agreement with our experimental results. An aromatic core twist in PDIs bearing one and two bromine substituents was also investigated by DFT. |
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Authors:
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Paramasivan Rajasingh; Revital Cohen; Elijah Shirman; Linda J W Shimon; Boris Rybtchinski |
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Publication Detail:
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Type: Journal Article Date: 2007-06-30 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Aug |
Date Detail:
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Created Date: 2007-07-27 Completed Date: 2007-09-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5973-9 Citation Subset: - |
Affiliation:
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Department of Organic Chemistry and Chemical Research Support Unit, Weizmann Institute of Science, Rehovot 76100, Israel. |
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