Journal article
A nearly quantitative synthetic approach towards monocyclic polystyrenes and the solvent, concentration and molecular weight effect on cyclic yield
Polymer (Guilford), v 101, pp 379-387
28 Sep 2016
Abstract
We report herein the effects of solvent, concentration, and molecular weight of α-alkynyl-ω-azido polystyrenes (l-PS-N3) on the synthesis of monocyclic polystyrenes (c-PS) by intra-chain coupling of l-PS-N3via Cu-catalyzed azide/alkyne cycloaddition method. By using fully end-functionalized l-PS-N3 as precursors, the optimum cyclization conditions to synthesize high purity c-PS (>99% by SEC) are revealed, at concentrations around 7.9 μmol/L in DMF. The c-PS products are fully characterized by SEC, LCCC, 1H NMR, and MALDI-TOF Mass spectrometry. The yield of c-PS decreases with increment of concentration of l-PS-N3 as predicted by Jacobson and Stockmayer's equation. Interestingly, among the three studied PS samples with different molecular weight (∼4k, 9k, 14k Da), the medium one (PS9k) provides the best c-PS yield, while in the three studied solvent (toluene, DMF, cyclohexane), DMF gives the best yied. The results reveal that the PS chain conformation in the solution, which is affected by the solvent and molecular weights, plays an important role in the intra-chain cyclization reaction.
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•Optimum cyclization conditions for the synthesis of high purity c-PS are revealed.•The effect of molecular weight, concentration and solvent is systematically studied.•The cyclization yield is greatly affected by the polymer chain conformation.
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Details
- Title
- A nearly quantitative synthetic approach towards monocyclic polystyrenes and the solvent, concentration and molecular weight effect on cyclic yield
- Creators
- Lingfeng Gao - Soochow UniversityJoongsuk Oh - Pohang University of Science and TechnologyTaihyun Chang - Pohang University of Science and TechnologyDongxue Chen - Soochow UniversityXiaohong Li - Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, ChinaXiaoming Yang - Soochow UniversityYingfeng Tu - Soochow UniversityXiulin Zhu - Soochow UniversityChristopher Y. Li - Drexel University
- Publication Details
- Polymer (Guilford), v 101, pp 379-387
- Publisher
- Elsevier
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Materials Science and Engineering
- Web of Science ID
- WOS:000384784800041
- Scopus ID
- 2-s2.0-84986005645
- Other Identifier
- 991019168507604721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Polymer Science