Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection
In this study, 2-(3-(hexyloxy)-5-methylphenoxy)-N-(4-nitrophenyl)acetamide (sensor L1) was synthesized and characterized by FT–IR, ESI–MS, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, elemental analysis, and single crystal X-ray techniques. The crystal structure and spa...
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MDPI AG
2021-06-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/11/6/671 |
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| author | Piangkwan Jansukra Tanwawan Duangthongyou Songwut Suramitr Kittipong Chainok Boontana Wannalerse |
| author_facet | Piangkwan Jansukra Tanwawan Duangthongyou Songwut Suramitr Kittipong Chainok Boontana Wannalerse |
| author_sort | Piangkwan Jansukra |
| collection | DOAJ |
| description | In this study, 2-(3-(hexyloxy)-5-methylphenoxy)-N-(4-nitrophenyl)acetamide (sensor L1) was synthesized and characterized by FT–IR, ESI–MS, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, elemental analysis, and single crystal X-ray techniques. The crystal structure and space group of sensor L1 was monoclinic and <i>P</i>2<sub>1</sub>, respectively. The crystal packing of sensor L1 was dominantly linked by two strong hydrogen bonds forming a six membered ring pattern. The binding properties of sensor L1 and various anions (F<sup>−</sup>, Cl<sup>−</sup>, Br<sup>−</sup>, CH<sub>3</sub>COO<sup>−</sup>, C<sub>6</sub>H<sub>5</sub>COO<sup>−</sup>, and H<sub>2</sub>PO<sub>4</sub><sup>−</sup>) were investigated by UV–Vis and <sup>1</sup>H NMR spectroscopy in DMSO. The proton resonance signals of sensor L1 and F<sup>−</sup> greatly changed positions when compared to those of anions. The solution color of sensor L1 changed from pale yellow to orange in the presence of F<sup>−</sup>. The UV–Vis results indicate that sensor L1 and F<sup>−</sup> ions underwent an internal charge transfer process. The stoichiometric complex was confirmed by Job’s method, revealing a 1:1 formation for sensor L1 and fluoride. Our results show that sensor L1 is highly selective for fluoride ions over other anions. |
| first_indexed | 2024-03-10T10:31:44Z |
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| language | English |
| last_indexed | 2024-03-10T10:31:44Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-e48f76c197e44045aa6eb3f50b5fd7b32023-11-21T23:39:35ZengMDPI AGCrystals2073-43522021-06-0111667110.3390/cryst11060671Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion DetectionPiangkwan Jansukra0Tanwawan Duangthongyou1Songwut Suramitr2Kittipong Chainok3Boontana Wannalerse4Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandMaterials and Textile Technology, Faculty of Science and Technology, Thammasat University, Pathum Thani 12120, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandIn this study, 2-(3-(hexyloxy)-5-methylphenoxy)-N-(4-nitrophenyl)acetamide (sensor L1) was synthesized and characterized by FT–IR, ESI–MS, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, elemental analysis, and single crystal X-ray techniques. The crystal structure and space group of sensor L1 was monoclinic and <i>P</i>2<sub>1</sub>, respectively. The crystal packing of sensor L1 was dominantly linked by two strong hydrogen bonds forming a six membered ring pattern. The binding properties of sensor L1 and various anions (F<sup>−</sup>, Cl<sup>−</sup>, Br<sup>−</sup>, CH<sub>3</sub>COO<sup>−</sup>, C<sub>6</sub>H<sub>5</sub>COO<sup>−</sup>, and H<sub>2</sub>PO<sub>4</sub><sup>−</sup>) were investigated by UV–Vis and <sup>1</sup>H NMR spectroscopy in DMSO. The proton resonance signals of sensor L1 and F<sup>−</sup> greatly changed positions when compared to those of anions. The solution color of sensor L1 changed from pale yellow to orange in the presence of F<sup>−</sup>. The UV–Vis results indicate that sensor L1 and F<sup>−</sup> ions underwent an internal charge transfer process. The stoichiometric complex was confirmed by Job’s method, revealing a 1:1 formation for sensor L1 and fluoride. Our results show that sensor L1 is highly selective for fluoride ions over other anions.https://www.mdpi.com/2073-4352/11/6/6713,5-dihydroxytoluene derivativehydrogen bonding interactionsingle crystal X-rayF<sup>−</sup> ion sensorsensor L1 |
| spellingShingle | Piangkwan Jansukra Tanwawan Duangthongyou Songwut Suramitr Kittipong Chainok Boontana Wannalerse Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection Crystals 3,5-dihydroxytoluene derivative hydrogen bonding interaction single crystal X-ray F<sup>−</sup> ion sensor sensor L1 |
| title | Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection |
| title_full | Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection |
| title_fullStr | Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection |
| title_full_unstemmed | Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection |
| title_short | Synthesis, Crystal Structure and Optical Properties of 2-(3-(Hexyloxy)-5-Methylphenoxy)-N-(4-Nitrophenyl)acetamide for Anion Detection |
| title_sort | synthesis crystal structure and optical properties of 2 3 hexyloxy 5 methylphenoxy n 4 nitrophenyl acetamide for anion detection |
| topic | 3,5-dihydroxytoluene derivative hydrogen bonding interaction single crystal X-ray F<sup>−</sup> ion sensor sensor L1 |
| url | https://www.mdpi.com/2073-4352/11/6/671 |
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