Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives
The development of polymeric materials with novel structures and unique properties and functionalities is of both academic and industrial significance. In this work, functional poly(dihalopentadiene)s were synthesized by boron trihalide-mediated multicomponent polymerization routes in a stereoselect...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-07-01
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| Series: | Polymers |
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| Online Access: | http://www.mdpi.com/2073-4360/10/8/821 |
| _version_ | 1811333653147418624 |
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| author | Ting Han Yun Zhang Benzhao He Jacky W. Y. Lam Ben Zhong Tang |
| author_facet | Ting Han Yun Zhang Benzhao He Jacky W. Y. Lam Ben Zhong Tang |
| author_sort | Ting Han |
| collection | DOAJ |
| description | The development of polymeric materials with novel structures and unique properties and functionalities is of both academic and industrial significance. In this work, functional poly(dihalopentadiene)s were synthesized by boron trihalide-mediated multicomponent polymerization routes in a stereoselective manner. The polymerizations of tetraphenylethylene-containing diyne, BX3 (X = Cl, Br) and p-tolualdehyde proceed smoothly in dichloromethane under mild conditions to afford high molecular weight poly(dihalopentadiene)s with a predominant (Z,Z)-configuration in moderate to good yields. The reaction conditions and the boron trihalide used were found to have great effects on the stereochemistry of the resulting polymer structures. The obtained poly(1,5-dihalo-(Z,Z)-1,4-pentadiene)s possess high thermal stability and good film-forming ability. Their thin films show high refractive index of 1.9007–1.6462 in a wide wavelength region of 380–890 nm with low optical dispersion. The polymers are weakly emissive in dilute solutions but become highly emissive upon aggregated, demonstrating a unique phenomenon of aggregation-enhanced emission. Their nanoaggregates in aqueous media can serve as sensitive fluorescent chemosensors for the detection of explosives with a superamplification effect and a low detection limit. |
| first_indexed | 2024-04-13T16:56:12Z |
| format | Article |
| id | doaj.art-c1b2146f6f5946deb489fc1a0dafed69 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-04-13T16:56:12Z |
| publishDate | 2018-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-c1b2146f6f5946deb489fc1a0dafed692022-12-22T02:38:48ZengMDPI AGPolymers2073-43602018-07-0110882110.3390/polym10080821polym10080821Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of ExplosivesTing Han0Yun Zhang1Benzhao He2Jacky W. Y. Lam3Ben Zhong Tang4HKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, ChinaHKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, ChinaHKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, ChinaHKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, ChinaHKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, ChinaThe development of polymeric materials with novel structures and unique properties and functionalities is of both academic and industrial significance. In this work, functional poly(dihalopentadiene)s were synthesized by boron trihalide-mediated multicomponent polymerization routes in a stereoselective manner. The polymerizations of tetraphenylethylene-containing diyne, BX3 (X = Cl, Br) and p-tolualdehyde proceed smoothly in dichloromethane under mild conditions to afford high molecular weight poly(dihalopentadiene)s with a predominant (Z,Z)-configuration in moderate to good yields. The reaction conditions and the boron trihalide used were found to have great effects on the stereochemistry of the resulting polymer structures. The obtained poly(1,5-dihalo-(Z,Z)-1,4-pentadiene)s possess high thermal stability and good film-forming ability. Their thin films show high refractive index of 1.9007–1.6462 in a wide wavelength region of 380–890 nm with low optical dispersion. The polymers are weakly emissive in dilute solutions but become highly emissive upon aggregated, demonstrating a unique phenomenon of aggregation-enhanced emission. Their nanoaggregates in aqueous media can serve as sensitive fluorescent chemosensors for the detection of explosives with a superamplification effect and a low detection limit.http://www.mdpi.com/2073-4360/10/8/821multicomponent polymerizationstereoselectivityaggregation-enhanced emissionexplosive detectionhigh refractive index |
| spellingShingle | Ting Han Yun Zhang Benzhao He Jacky W. Y. Lam Ben Zhong Tang Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives Polymers multicomponent polymerization stereoselectivity aggregation-enhanced emission explosive detection high refractive index |
| title | Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives |
| title_full | Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives |
| title_fullStr | Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives |
| title_full_unstemmed | Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives |
| title_short | Functional Poly(dihalopentadiene)s: Stereoselective Synthesis, Aggregation-Enhanced Emission and Sensitive Detection of Explosives |
| title_sort | functional poly dihalopentadiene s stereoselective synthesis aggregation enhanced emission and sensitive detection of explosives |
| topic | multicomponent polymerization stereoselectivity aggregation-enhanced emission explosive detection high refractive index |
| url | http://www.mdpi.com/2073-4360/10/8/821 |
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