Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers
Abstract Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull mole...
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag
2021-04-01
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| Series: | Organic Materials |
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| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725075 |
| _version_ | 1818603046286917632 |
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| author | Irina Zharinova Nicolau Saker Neto Tze Cin Owyong Jonathan M. White Wallace W. H. Wong |
| author_facet | Irina Zharinova Nicolau Saker Neto Tze Cin Owyong Jonathan M. White Wallace W. H. Wong |
| author_sort | Irina Zharinova |
| collection | DOAJ |
| description | Abstract
Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull molecules were generated upon deprotonation of the phenol leading to large redshifts in absorbance maxima. UV-vis absorbance studies also revealed strong dependence of the band position on solvent polarity: a smooth bathochromic shift can be observed with the decrease of the solvent polarity. The molecule with one p-phenylene bridging unit showed the strongest solvatochromic characteristics in the series, spanning the range of 167 nm while moving from polar water to less polar N,N-dimethylformamide. The magnitude of this shift was close to Reichardt's dye — one of the most solvatochromic organic dyes known. |
| first_indexed | 2024-12-16T13:16:56Z |
| format | Article |
| id | doaj.art-f69c41c5f3514c209c2f9fb07ee4681d |
| institution | Directory Open Access Journal |
| issn | 2625-1825 |
| language | English |
| last_indexed | 2024-12-16T13:16:56Z |
| publishDate | 2021-04-01 |
| publisher | Georg Thieme Verlag |
| record_format | Article |
| series | Organic Materials |
| spelling | doaj.art-f69c41c5f3514c209c2f9fb07ee4681d2022-12-21T22:30:27ZengGeorg Thieme VerlagOrganic Materials2625-18252021-04-01030210311810.1055/s-0041-1725075Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) SpacersIrina Zharinova0Nicolau Saker Neto1Tze Cin Owyong2Jonathan M. White3Wallace W. H. Wong4ARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, AustraliaARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, AustraliaARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, AustraliaARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, AustraliaARC Centre of Excellence in Exciton Science, School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Victoria 3010, AustraliaAbstract Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull molecules were generated upon deprotonation of the phenol leading to large redshifts in absorbance maxima. UV-vis absorbance studies also revealed strong dependence of the band position on solvent polarity: a smooth bathochromic shift can be observed with the decrease of the solvent polarity. The molecule with one p-phenylene bridging unit showed the strongest solvatochromic characteristics in the series, spanning the range of 167 nm while moving from polar water to less polar N,N-dimethylformamide. The magnitude of this shift was close to Reichardt's dye — one of the most solvatochromic organic dyes known.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725075conjugated moleculescross-couplingelectron donor–acceptor systemssolvatochromism |
| spellingShingle | Irina Zharinova Nicolau Saker Neto Tze Cin Owyong Jonathan M. White Wallace W. H. Wong Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers Organic Materials conjugated molecules cross-coupling electron donor–acceptor systems solvatochromism |
| title | Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers |
| title_full | Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers |
| title_fullStr | Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers |
| title_full_unstemmed | Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers |
| title_short | Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers |
| title_sort | synthesis and solvatochromic behavior of zwitterionic donor bridge acceptor systems with oligo p phenylene spacers |
| topic | conjugated molecules cross-coupling electron donor–acceptor systems solvatochromism |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1725075 |
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