Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection
Abstract
:1. Introduction
2. Experiment
2.1. Materials
2.2. Methods
Crystallographic Methods
2.3. Apparatus
2.4. The Synthesis of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate, Sensor R1, as Shown in Scheme 1
3. Results and Discussion
3.1. Crystal Structure of Sensor R1
3.2. The Binding Behavior of Sensor R1 and Different Anions Characterized by 1H-NMR Spectroscopy
3.3. Characterization of the Binding Interaction of Sensor R1 and Different Anions by UV-Vis Spectroscopy
3.4. Complexation Study of Sensor R1 and Various Anions by Fluorescence Spectroscopy
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
References
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Crystal Data | Sensor R1 |
---|---|
Empirical formula | C18H19NO6S |
Formula weight | 377.40 |
Temperature(K) | 296 |
Crystal system | monoclinic |
Space group | P21/c |
a/Å | 8.1631(3) |
b/Å | 9.3968(3) |
c/Å | 23.5699(9) |
α/° | 90.00 |
β/° | 97.8630(10) |
γ/° | 90.00 |
Volume/Å3 | 1790.98(11) |
Z | 4 |
ρcalc g/cm3 | 1.400 |
μ/mm−1 | 0.216 |
F (000) | 792.0 |
Crystal size/mm3 | 0.24 × 0.2 × 0.1 |
Radiation | MoKα (λ = 0.71073) |
2Θ range for data collection/° | 4.672 to 54.968 |
Index ranges | −10 ≤ h ≤ 10, −12 ≤ k ≤ 12, −30 ≤ l ≤ 30 |
Reflections collected | 36,616 |
Independent reflections | 4106 [Rint = 0.0773, Rsigma = 0.0345] |
Data/restraints/parameters | 4106/12/254 |
Goodness-of-fit on F2 | 1.017 |
Final R indexes [I ≥ 2σ (I)] | R1 = 0.0451, wR2 = 0.0965 |
Final R indexes [all data] | R1 = 0.0797, wR2 = 0.1141 |
Largest diff. peak/hole/e Å−3 | 0.14/−0.31 |
Sensor R1 | |||||||
---|---|---|---|---|---|---|---|
Selected bond lengths | |||||||
N1–C17 | 1.468(4) | C1–O1 | 1.421(2) | C5–O5 | 1.367(2) | S1–O2 | 1.430(2) |
N1–C18 | 1.460(3) | C3–O4 | 1.370(2) | S1–O1 | 1.594(2) | S1–O3 | 1.418(2) |
Selected bond angles | |||||||
C12–N1–C18 | 116.1(2) | O1–S1–O3 | 103.02(9) | ||||
C17–N1–C12 | 112.7(2) | O2–S1–O3 | 118.5(1) | ||||
C17–N1–C18 | 109.6(2) | S1–O1–C1 | 118.5(1) | ||||
C7–S1–O1 | 102.31(9) | O4–C3–C2 | 117.3(2) | ||||
C7–S1–O2 | 109.2(1) | O4–C3–C4 | 121.3(2) | ||||
C7–S1–O3 | 113.3(1) | O5–C5–C4 | 117.7(2) | ||||
O1–S1–O2 | 108.93(9) | O5–C5–C6 | 121.3(2) | ||||
Selected torsion angles | |||||||
C17–N1–C12–C11 | −110.0(3) | O3–S1–C7–C8 | −49.9(2) | ||||
C17–N1–C12–C13 | 71.1(3) | O3–S1–C7–C16 | 135.2(2) | ||||
C18–N1–C12–C11 | 17.5(3) | S1–O1–C1–C2 | 70.2(2) | ||||
C18–N1–C12–C13 | −161.4(2) | S1–O1–C1–C6 | −111.3(2) | ||||
O2–S1–O1–C1 | −66.5(2) | O5–C5–C4–C3 | −179.5(2) | ||||
O2–S1–O7–C8 | 175.6(2) | O5–C5–C6–C1 | −179.8(2) | ||||
O2–S1–O7–C16 | 0.7(2) | O4–C3–C2–C1 | 179.0(2) | ||||
O3–S1–O1–C1 | 166.8(1) | O4–C3–C4–C5 | −179.9(2) |
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Khunarj, S.; Saijaroensakul, W.; Marom, W.; Chainok, K.; Duangthongyou, T.; Pinchaipat, B.; Wannalerse, B. Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection. Crystals 2022, 12, 1836. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst12121836
Khunarj S, Saijaroensakul W, Marom W, Chainok K, Duangthongyou T, Pinchaipat B, Wannalerse B. Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection. Crystals. 2022; 12(12):1836. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst12121836
Chicago/Turabian StyleKhunarj, Siraprapa, Woradorn Saijaroensakul, Wilailak Marom, Kittipong Chainok, Tanwawan Duangthongyou, Bussaba Pinchaipat, and Boontana Wannalerse. 2022. "Synthesis, Crystal Structure and Optical Properties of 3,5-Dihydroxyphenyl-5-(dimethylamino)naphthalene-1-sulfonate as a Fluorescence Sensor for Fluoride Ion Detection" Crystals 12, no. 12: 1836. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst12121836