Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent
To construct novel ion receptors and D-A self-assembly systems for materials with better functions, the annulation of a tetrathiafulvalene donor with a magnesium norphthalocyanine core via a flexible tetrathiacrown ether bridge afforded a new triad <b>1</b>. The structure of this product...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/3/916 |
| _version_ | 1827759917705986048 |
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| author | Ruibin Hou Xiaoyu Liu Yan Xia Dongfeng Li |
| author_facet | Ruibin Hou Xiaoyu Liu Yan Xia Dongfeng Li |
| author_sort | Ruibin Hou |
| collection | DOAJ |
| description | To construct novel ion receptors and D-A self-assembly systems for materials with better functions, the annulation of a tetrathiafulvalene donor with a magnesium norphthalocyanine core via a flexible tetrathiacrown ether bridge afforded a new triad <b>1</b>. The structure of this product was characterized by 1H NMR and infrared spectroscopy, time-of-flight mass spectrometry, and elemental analysis. The optical and electrochemical properties were investigated using UV–vis spectroscopy and cyclic voltammetry. The complex of triad <b>1</b> and 2,3,5,6- tetrafluoro-7,7,8,8-tetracyanoquinodimethane produced electron transfer with a radical cationic character, as confirmed by UV–Vis and electron paramagnetic resonance analysis. Furthermore, the target compound presented evident intramolecular charge-transfer interactions in ground states, which were explained using density functional theory. Furthermore, norphthalocyanine <b>1</b> was able to coordinate Ag<sup>+</sup> through the peripheral ligating oxathiaether crown. |
| first_indexed | 2024-03-11T09:34:22Z |
| format | Article |
| id | doaj.art-5a0aef3911d64db4989974ba61773e57 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:34:22Z |
| publishDate | 2023-01-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5a0aef3911d64db4989974ba61773e572023-11-16T17:24:59ZengMDPI AGMolecules1420-30492023-01-0128391610.3390/molecules28030916Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene SubstituentRuibin Hou0Xiaoyu Liu1Yan Xia2Dongfeng Li3School of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, ChinaSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, ChinaSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, ChinaSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, ChinaTo construct novel ion receptors and D-A self-assembly systems for materials with better functions, the annulation of a tetrathiafulvalene donor with a magnesium norphthalocyanine core via a flexible tetrathiacrown ether bridge afforded a new triad <b>1</b>. The structure of this product was characterized by 1H NMR and infrared spectroscopy, time-of-flight mass spectrometry, and elemental analysis. The optical and electrochemical properties were investigated using UV–vis spectroscopy and cyclic voltammetry. The complex of triad <b>1</b> and 2,3,5,6- tetrafluoro-7,7,8,8-tetracyanoquinodimethane produced electron transfer with a radical cationic character, as confirmed by UV–Vis and electron paramagnetic resonance analysis. Furthermore, the target compound presented evident intramolecular charge-transfer interactions in ground states, which were explained using density functional theory. Furthermore, norphthalocyanine <b>1</b> was able to coordinate Ag<sup>+</sup> through the peripheral ligating oxathiaether crown.https://www.mdpi.com/1420-3049/28/3/916tetrathiafulvalenenorphthalocyaninetetrathiacrown etherintramolecular charge-transferdensity functional theory |
| spellingShingle | Ruibin Hou Xiaoyu Liu Yan Xia Dongfeng Li Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent Molecules tetrathiafulvalene norphthalocyanine tetrathiacrown ether intramolecular charge-transfer density functional theory |
| title | Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent |
| title_full | Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent |
| title_fullStr | Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent |
| title_full_unstemmed | Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent |
| title_short | Synthesis and Properties of Norphthalocyanines Functionalized with a Tetrathiacrown Ether–Tetrathiafulvalene Substituent |
| title_sort | synthesis and properties of norphthalocyanines functionalized with a tetrathiacrown ether tetrathiafulvalene substituent |
| topic | tetrathiafulvalene norphthalocyanine tetrathiacrown ether intramolecular charge-transfer density functional theory |
| url | https://www.mdpi.com/1420-3049/28/3/916 |
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