Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection
3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate, also referred to as sensor R1, was synthesized and characterized by <sup>1</sup>H- and <sup>13</sup>C-NMR, IR, HRMS, and single-crystal X-ray diffraction. Connections in the packing crystal structure of sensor R1 o...
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MDPI AG
2022-12-01
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| author | Siraprapa Khunarj Woradorn Saijaroensakul Wilailak Marom Kittipong Chainok Tanwawan Duangthongyou Bussaba Pinchaipat Boontana Wannalerse |
| author_facet | Siraprapa Khunarj Woradorn Saijaroensakul Wilailak Marom Kittipong Chainok Tanwawan Duangthongyou Bussaba Pinchaipat Boontana Wannalerse |
| author_sort | Siraprapa Khunarj |
| collection | DOAJ |
| description | 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate, also referred to as sensor R1, was synthesized and characterized by <sup>1</sup>H- and <sup>13</sup>C-NMR, IR, HRMS, and single-crystal X-ray diffraction. Connections in the packing crystal structure of sensor R1 occur through hydrogen bonding interactions. However, no π-π stacking interactions between molecules of sensor R1 were observed. Addition of fluoride ion to a solution of sensor R1 resulted in the appearance of a new absorption band at 310 nm, which corresponded to the deprotonated species, and quenching of the peak at an emission wavelength of 562 nm. For the addition of other anions, there was a slight decrease in corresponding peaks in the UV-visible and emission spectra of sensor R1. According to the <sup>1</sup>H-NMR study, the aromatic proton resonances of sensor R1 shifted upfield when adding fluoride ion. Analysis of the solutions prepared using Job’s method revealed that the complexation ratio of the complex formed between sensor R1 and fluoride ion was 1:1. The Stern−Volmer quenching constant (K<sub>sv</sub>) between sensor R1 and fluoride ion was characterized as 7157 M<sup>−1</sup>. |
| first_indexed | 2024-03-09T17:09:06Z |
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| id | doaj.art-2e2609c648f54fbcbe45ac0b36f76a72 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T17:09:06Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-2e2609c648f54fbcbe45ac0b36f76a722023-11-24T14:11:49ZengMDPI AGCrystals2073-43522022-12-011212183610.3390/cryst12121836Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion DetectionSiraprapa Khunarj0Woradorn Saijaroensakul1Wilailak Marom2Kittipong Chainok3Tanwawan Duangthongyou4Bussaba Pinchaipat5Boontana Wannalerse6Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, ThailandDepartment of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Naresuan University, Phitsanulok 65000, ThailandDepartment of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, Thailand3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate, also referred to as sensor R1, was synthesized and characterized by <sup>1</sup>H- and <sup>13</sup>C-NMR, IR, HRMS, and single-crystal X-ray diffraction. Connections in the packing crystal structure of sensor R1 occur through hydrogen bonding interactions. However, no π-π stacking interactions between molecules of sensor R1 were observed. Addition of fluoride ion to a solution of sensor R1 resulted in the appearance of a new absorption band at 310 nm, which corresponded to the deprotonated species, and quenching of the peak at an emission wavelength of 562 nm. For the addition of other anions, there was a slight decrease in corresponding peaks in the UV-visible and emission spectra of sensor R1. According to the <sup>1</sup>H-NMR study, the aromatic proton resonances of sensor R1 shifted upfield when adding fluoride ion. Analysis of the solutions prepared using Job’s method revealed that the complexation ratio of the complex formed between sensor R1 and fluoride ion was 1:1. The Stern−Volmer quenching constant (K<sub>sv</sub>) between sensor R1 and fluoride ion was characterized as 7157 M<sup>−1</sup>.https://www.mdpi.com/2073-4352/12/12/1836hydrogen bondingfluoride ionsensor |
| spellingShingle | Siraprapa Khunarj Woradorn Saijaroensakul Wilailak Marom Kittipong Chainok Tanwawan Duangthongyou Bussaba Pinchaipat Boontana Wannalerse Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection Crystals hydrogen bonding fluoride ion sensor |
| title | Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection |
| title_full | Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection |
| title_fullStr | Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection |
| title_full_unstemmed | Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection |
| title_short | Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection |
| title_sort | synthesis crystal structure and optical properties of 3 5 dihydroxyphenyl 5 dimethylamino naphthalene 1 sulfonate as a fluorescence sensor for fluoride ion detection |
| topic | hydrogen bonding fluoride ion sensor |
| url | https://www.mdpi.com/2073-4352/12/12/1836 |
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