A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure

Chantaniyomporn, Kanokporn; Charoensuk, Kiratikarn; Duangthongyou, Tanwawan; Chainok, Kittipong; Wannalerse, Boontana

doi:10.3390/cryst14110943

Open AccessArticle

A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure

by

Kanokporn Chantaniyomporn

¹,

Kiratikarn Charoensuk

¹,

Tanwawan Duangthongyou

²

,

Kittipong Chainok

³

and

Boontana Wannalerse

^2,*

¹

Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

²

Center of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

³

Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, Thailand

^*

Author to whom correspondence should be addressed.

Crystals 2024, 14(11), 943; https://doi.org/10.3390/cryst14110943

Submission received: 9 October 2024 / Revised: 28 October 2024 / Accepted: 28 October 2024 / Published: 30 October 2024

(This article belongs to the Section Inorganic Crystalline Materials)

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Abstract

:

2′-(hexyloxy)-[1,1′-biphenyl]-2-yl 5-(dimethylamino)naphthalene-1-sulfonate (KC1) was synthesized by using biphenol and dansyl chloride as starting materials. The KC1 was characterized via single X-ray diffraction, FTIR, HRMS and ¹H and ¹³C-NMR. The KC1 indicates triclinic as P1 in the space group type. From the KC1, the biphenolic backbone structure is twisted at an angle of 54.48° due to connecting the dansyl unit and hexyl moiety. Upon the addition of the Fe³⁺ ion to the KC1 solution, the fluorescence emission at 585 nm of KC1 was quenched due to complexation between KC1 and the Fe³⁺ ion. The complexation ratio of KC1 and Fe³⁺ was determined to be a 1:1 formation via Job’s analysis. The Stern–Volmer constant (K_sv) calculated was 21,203 M⁻¹ for the KC1 and the Fe³⁺ ion complex.

Keywords:

biphenolic compound; Fe³⁺ sensor; quench

1. Introduction

Crystal ligands have been designed and synthesized for many applications, such as sensors and molecular tags. These ligands contain the nitrogen, oxygen and sulfur donor atoms that are important parts of binding sites for metal ion coordination complexes [1,2,3,4]. The coordinated complexes formed from ligands and specific metal ions lead to changes in optical and electronic properties. There are many coordination processes, such as cheated quenching/enhancing fluorescence, internal charge transfer and photo-induced electron transfer [5,6,7,8,9]. These mechanisms are essential for sensitivity and selectivity during metal complexation. Metal ions are found everywhere in daily life and have essential uses in biological, environmental and industrial fields. However, some metal ions are toxic and harmful to humans upon excessive intake [10,11,12,13,14,15,16]. Currently, many researchers are focused on synthesizing fluorescence sensor molecules that are specifically coordinated to metal ions. Among metal ions, iron (Fe) is an important transition element that plays many roles, such as in metabolism and oxygen carrying and catalysis. The Fe³⁺ ion is greater in natural abundance rather than other oxidation states due to its stability. For the human body, a lack of iron is linked to many diseases and disorders [17,18,19], and metal fluorescence detection is an easier and quicker technique than other methods to diagnose deficiencies. Moreover, the advantages of the fluorescence method include being able to detect metal ions in aqueous samples and in vivo cells [20,21]. For example, Areti et. al. (2016) [4] prepared triazole-connected quinolone based on glucopyranose binding to Zn²⁺ and Cd²⁺ producing an enhancement in fluorescence, but Cd²⁺ changed to quench fluorescence. Moreover, this molecule can be generated via INHIBIT and IMPLICATION logic gates for Zn²⁺-H₂PO₄⁻ and Hg²⁺-CN⁻, respectively. Zhang et. al. (2018) [15] prepared a new luminescent MOF, [Cd₂(pbdc)(H₂O)₃], containing the 5-phosphonobenzene-1,3-dicarboxylic acid (H₄pbdc) ligand as [Cd₂(pbdc)(H₂O)₃], which linked three dimensions. With the addition of Cu²⁺, Al³⁺ and Fe³⁺ ions, the fluorescence intensity of [Cd₂(pbdc)(H₂O)₃] was more obviously quenched than with other metal ions, meaning that this MOF has higher sensitivity and selectivity for Cu²⁺, Al³⁺ and Fe³⁺ ions in aqueous solution systems. Rasin et. al. (2022) [22] synthesized a fluorescence sensor containing benzene-1,2-diamine and pyrene moieties in DMSO:H₂O (9.5/5 v/v) for Fe³⁺ ion detection, with the addition of the Fe³⁺ ion increasing the quench fluorescence when compared to other metal ions. This process occurred under photo-induced electron transfer. For this research, we described the synthesis, crystal structure and fluorescence properties of KC1 and investigated the sensitivity and selectivity for metal ions.

2. Experimental Section

2.1. Material

For all reagents in the experiment, 2,2′-biphenol was purchased from Sigma-Aldrich (St. Louis, MO, USA). Potassium carbonate was purchased from Carlo Erba Reagents S.A.S. (Val de Reuil, France). 1-bromahexane and dansyl chloride were purchased from Tokyo Chemical Industry Company Limited (Tokyo, Japan). Iron(III) nitrate nonahydrate, zinc(II) nitrate hexahydrate, copper(II) nitrate trihydrate, nickel(II) nitrate hexahydrate, lead(II) nitrate and mercury(II) nitrate monohydrate were purchased from QRëC, New Zealand. Dichloromethane, dimethyl sulfoxide, hexane and acetonitrile were purchased from RCI Labscan Limited (Bangkok, Thailand).

2.2. Apparatus

The Fourier transform infrared technique (FTIR) was used to examine the functional groups within compounds using a Spectrum Two FT-IR Perkin Elmer spectrometer, Waltham, MA, USA. An FL8500 Fluorescence Perkin Elmer spectrometer was used to investigate the binding behavior of KC1 and metal ions. ¹H-¹³C NMR spectroscopy was utilized to study the structures of synthesized compounds using a 400 MHz NMR Bruker spectrometer, Madison, WI, USA. HRMS was utilized to investigate the parent peak using a nano-LC quadrupole time-of-flight high-resolution mass spectrophotometer.

2.3. X-Ray Crystallography

CCDC 2361572 is the crystallographic data for KC1 accessed on 10 June 2024. These data can be provided from http://www.ccdc.cam.ac.uk. Crystal data of KC1 were collected on a Bruker D8 QUEST CMOS PHOTONII, Germany, and combined with graphite monochromated Mo-Kα(λ = 0.71073Å) radiation at 296 K. In addition, the KCl structure was solved using the ShelXT [23] structure solution program with included Pattererson and dual space recycling methods, and was also performed using least squares with ShelXL [24]. All hydrogen atoms were treated by calculation [25]. The crystal data of KC1are listed in Table 1. Mercury software (http://www.ccdc.cam.ac.uk) was used to depict the KC1 molecule [26,27].

2.4. Fluorescence Titration

The solvent used in the fluorescence experiment was DMSO:H₂O (7/3 v/v). The stock solution of KC1 in a concentration of 1 × 10⁻³ M was prepared. Then, the KC1 solution was diluted to 1 × 10⁻⁵ M in DMSO:H₂O (7/3 v/v). Metal ions were added to prepare KC1 solution in a concentration of 0–3000 equivalents. Then, the emission spectra of fluorescence titration were recorded at 350–800 nm.

2.5. Synthesis of 2′-(Hexyloxy)-[1,1′-Biphenyl]-2-yl 5-(Dimethylamino)Naphthalene-1-Sulfonate, KC1 Exhibited in Scheme 1

2.5.1. 2′-(Hexyloxy)-[1,1′-Biphenyl]-2-ol, (C₁₈H₂₂O₂) Compound A

2,2′-biphenol (3 g, 16.1 mmol) and potassium carbonate (K₂CO₃) (2.226 g, 16.1 mmol) in 30 mL CH₃CN were stirred and refluxed at 130 °C under an N₂ atmosphere for 1 h. 1-bromo hexane (2.259 mL, 16.1 mmol) in 50 CH₃CN was added dropwise with an additional funnel. Then, the mixture reaction was refluxed for 4 h at 130 °C under N₂. The reaction mixture reaction was evaporated and then extracted with dichloromethane and distilled water. The organic layer was without water after using sodium sulfate. The product was purified via column chromatography with CH₂Cl₂ as an eluent, affording a colorless liquid in the percentage yield of 80.6 (3.513 g). ¹H-NMR (CDCl₃): δ 7.41 (ddd, J = 7.7, 6.3, 1.9 Hz, 2H), 7.38–7.32 (m, 2H), 7.17 (td, J = 7.5, 1.1 Hz, 1H), 7.13–7.03 (m, 3H), 6.70 (s, 1H), 4.11 (t, J = 6.6 Hz, 2H), 1.79 (dt, J = 14.6, 6.7 Hz, 2H), 11.47–1.37 (m, 2H), 1.32 (tt, J = 5.5, 2.7 Hz, 4H), 0.96–0.87 (m, 3H). ¹³C-NMR(CDCl₃): δ 155.09, 154.12, 132.63, 131.46, 129.23, 128.06, 126.75, 122.42, 121.01, 117.80, 113.45, 69.93, 31.50, 29.13, 25.56, 22.62, 14.08. IR (cm⁻¹): 1226, 1497, 1572, 2858, 2930, 3382. HRMS(m/z): C₁₈H₂₂O₂Na was calculated to be 293.1517 and found to be 293.1543 (M + Na)⁺.

2.5.2. 2′-(Hexyloxy)-[1,1′-Biphenyl]-2-yl 5-(Dimethylamino)Naphthalene-1-Sulfonate, C₃₀H₃₃NO₄S (KC1)

Compound A (3.5 g, 11.9 mmol) and potassium carbonate (K₂CO₃) (1.789 g, 12.9 mmol) in 30 mL CH₃CN were refluxed at 130 °C under an N₂ atmosphere for 1 h. Then, dansyl chloride (2.259 mL, 8.37 mmol) in 50 mL CH₃CN was added drop by drop using an additional funnel. Next, the reaction mixture was refluxed at 130 °C for 4 h under an N₂ atmosphere. The mixture was evaporated by rotary evaporator and then extracted three times by using dichloromethane and distilled water. For extraction, the organic layer was produced without water by using sodium sulfate. Column chromatography using hexane: dichloromethane (3:7 v/v) as an eluent was added to purify the product, affording a yellow solid with a percentage yield of 42.03 (1.918 g). ¹H-NMR(CDCl₃): δ 8.50 (s, 1H), 8.09 (s, 1H), 7.87 (s, 1H), 7.42 (s, 1H), 7.42 (s, 1H), 7.35 (s, 1H), 7.28 (s, 1H), 7.20 (s, 2H), 7.15 (dd, J = 7.6, 0.9 Hz, 2H), 6.93–6.87 (m, 2H), 6.81 (d, 1H), 6.53 (d, J = 14.9 Hz, 1H), 6.43 (d, 1H), 2.91 (m, 6H), 3.67 (t, 2H), 1.53 (q, 2H), 1.36–1.16 (m, 6H), 1.36–1.16 (m, 1H), 0.91 (t, 3H). ¹³C NMR(CDCl₃): δ 155.65, 132.63, 130.67, 129.95, 129.79, 128.53, 128.23, 126.61, 119.95, 119.61, 115.26, 111.13, 147.65, 132.63, 132.10, 128.53, 128.34, 125.62, 123.20, 122.78, 119.95, 115.26, 67.87, 31.48, 29.04, 25.55, 22.58, 14.02, 45.52. IR (cm⁻¹): 1095, 1234, 1364, 1152, 1465, 1570, 2858, 2934. HRMS (m/z): C₃₀H₃₃NO₄SNa was calculated to be 526.2028 and found to be 526.2057 (M + Na)⁺.

3. Results and Discussion

3.1. The Crystallographic Structure Detail of Sensor KC1

The KC1 in the dichloromethane solvent was grown in crystals. An asymmetric unit of KC1 consists of one molecule of KC1, biphenol with two substitutional groups on hydroxyl groups and dansyl and hexyl groups (Figure 1). The two aromatic rings of biphenyl moiety are not coplanar. The dihedral angle between the two aromatic rings is 54.48°. This may have an effect on the steric interactions of the hexyl and dansyl groups. As a result, the naphthalene plane of the dansyl group aligns in parallel with one phenyl plane. The hexyl moiety is in the zigzag form. The torsion angle between hexyl and one phenol ring is 8.37° (C23-C24-O4-C25), while that between another phenol and dansyl unit is 103.17° (C18-C13-O3-S1). The two adjacent molecules showed that the molecule structures are stabilized by a C-H···O interaction between an oxygen atom of phenol and a hydrogen atom of a hexyl moiety (O4---H28-C28) at a distance of 2.678 Å as shown in Table 2. Furthermore, these two adjacent molecules are further assembled by van der Waals forces to form a 1D structure the along diagonal of the bc plane, shown in Figure 2. In addition, the crystal structure of KC1 was stabilized by using another C-H···O interaction at a distance of 2.668 Å between a dansyl oxygen atom in the 1D structure and a phenol hydrogen atom (O1---H22-C22) in the other 1D chain to contribute a 2D structure in the bc plane, as shown in Figure 3. This 2D layer is further stabilized by van der Waals forces to support the 3D structure.

3.2. An Investigation of the Binding Behavior of KC1 and Metal Ions by Using a Fluorescence Technique

The emission wavelength of KC1 displayed a maximum at 585 nm, and there was another wavelength at 700 nm in DMSO:H₂O (7:3 v/v). Upon the addition of the Fe³⁺ ion to the KC1 solution in the equivalent concentration range of 0–3000, the emission bands of KC1 at 585 and 700 nm are quenched due to the Fe³⁺ ion complex directly binding to KC1 (Figure 4) [22]. Upon the addition of different metal ions, the fluorescence emission at 585 gradually decreased, as depicted in Figure S2 (see Supplementary Materials). Results from the fluorescence titration indicated that KC1 was selective regarding the Fe³⁺ ion rather than the other metal ions. In the case of other metal ions, the KC1 showed a weak interaction, with the emission wavelength at 585 nm representing a small change. The maximum intensity ratio between KC1 and Fe³⁺ ions was shown to be 0.5 by using Job’s method, and a complex between KC1 and Fe³⁺ ions at a 1:1 ratio formation is shown in Figure 5 [28,29]. Moreover, there was only a color change of KC1 and Fe³⁺ ions under a UV lamp at 365 nm. For other metal ions, the color stayed the same, as shown in Figure 6. This result suggested that KC1 was obviously selective to the Fe³⁺ ion. The Stern–Volmer plot of complexation between KC1 and the Fe³⁺ ion is shown in Figure 7. The Stern–Volmer constant (K_sv) was evaluated as 21,203 M⁻¹. Furthermore, the sensitivity and selectivity of the complexation between KC1 and the Fe³⁺ ion was investigated by analyzing the competition of various metal ions in the solution, as shown in Figure 8. It was found that KC1 and Fe³⁺ exhibited quench fluorescence, but KC1 and other metal ions still displayed the fluorescence’s blue bar graph. For KC1-Fe³⁺ and various metal ions, the orange bar graph indicated that there was no fluorescence emission at 585 nm, meaning there was no effect when adding other metal ions into the KC1-Fe³⁺ solution. Therefore, KC1 has the ability to detect Fe³⁺ while mixed with other metal ions in a solution. Furthermore, the limit of detection (LOD) between KC1 and the Fe³⁺ ion was evaluated as being 0.74 μM [28,29].

3.3. The Binding Mode Between KC1 and Fe³⁺ Ion via FTIR Spectroscopy

The FTIR spectra of KC1 and mixing KC1 with Fe³⁺ by using the ATR mode for analysis are shown in Figure 9. For the KC1 solid, the main function groups and wavenumber in units of cm⁻¹ are represented by a red line and are also listed in Table 3.

In addition to mixing KC1 and the Fe³⁺ ion (black line), it was found that the strong shoulder between 3000 cm⁻¹ and 4000 cm⁻¹ exhibited –OH stretching of H₂O belonging to Fe(NO)₃.9H₂O, and the wavenumber of the -S=O group at 1234 cm⁻¹ moved to 1277 cm⁻¹, indicating the oxygen atom position of the -S=O group and showing that KC1 was directly bound to the Fe³⁺ ion.

3.4. Application of KC1 and Various Concentrations of Fe³⁺ Ions on TLC Plates

The TLC plates with coated-KC1 were evaluated regarding the detection of Fe³⁺ ions in various concentrations, as shown in Figure 10. The result showed that only KC1 displayed yellow brightness on a TLC plate. The color of KC1 on TLC plates changed to a pale yellow upon the addition of the 1 and 5 equivalents, as shown in Figure 10. Furthermore, after the addition of the 10 equiv. to the coated-KC1 on the TLC plate, the yellow brightness of KC1 darkened. The TLC plates with coated-KC1 were utilized to detect the Fe³⁺ ion.

4. Conclusions

The KC1 sensor was successfully synthesized in two steps. From the KC1 structure, it was found that the two linked molecules are connected and stabilized by the C-H···O interaction. Upon adding the Fe³⁺ ion to the KC1 solution, it was found that the KC1 emission band was quenched under the complex formation between KC1 and the Fe³⁺ ion. IR results indicated that the KC1 binding mode at the oxygen atom (S=O group) interacted with the Fe³⁺ ion. Moreover, the coated-KC1 on the TLC plate has the ability to fluorescence quench for Fe³⁺ ion detection. Therefore, KC1 has the ability to detect the Fe³⁺ ion when among other metal ions.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/cryst14110943/s1, Figure S1: ¹H-NMR spectra of KC1 in d-CDCl₃; Figure S2: Fluorescence titration between KC1 (1 × 10⁻⁵ M) and Ni²⁺ ion (0–3000 eq) in DMSO:H₂O (7:3 v/v).

Author Contributions

Conceptualization, B.W.; methodology, B.W.; funding, B.W.; writing draft, B.W.; writing, T.D.; methodology, K.C. (Kanokporn Chantaiyomporn), K.C. (Kiratikarn Charoensuk) and K.C (Kittipong Chainok). All authors have read and agreed to the published version of the manuscript.

Funding

The authors would like to thank the Kasetsart University Research and Development (KURDI) for financial support.

Data Availability Statement

The original contributions presented in the study are included in the article/Supplementary Material, further inquiries can be directed to the corresponding author/s.

Acknowledgments

The authors thank the Department of Chemistry, Faculty of Science, Kasetsart University, for providing equipment and facilities.

Conflicts of Interest

The authors declare no conflict of interest.

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Scheme 1. The synthetic pathway for KC1 sensor.

Figure 1. Labelled atoms in the asymmetric unit of KC1.

Figure 2. The 1D structure of KC1 along the diagonal of the bc plane.

Figure 3. The 2D structure of KC1 along the bc plane.

Figure 4. The fluorescence titration between KC1 (1 × 10⁻⁵ M) and Fe³⁺ ions (0–3000 eq) in DMSO:H₂O (7:3 v/v) (Host is the KC1).

Figure 5. Job’s analysis of KC1 and Fe³⁺ in DMSO:H₂O (7:3 v/v).

Figure 6. The color change of KC1 (1 × 10⁻³ M) (A) with metal ions (3000 equiv.): (B) Pb²⁺, (C) Ni²⁺, (D) Zn²⁺, (E) Cu²⁺, (F) Co²⁺, (G) Fe³⁺ and (H) Hg²⁺ in DMSO: H₂O (7:3 v/v).

Figure 7. The plot graph of Stern–Volmer between KC1 and Fe³⁺ ions in DMSO:H₂O (7:3 v/v).

Figure 8. The competitive metal ions (Hg²⁺, Pb²⁺, Zn²⁺, Cu²⁺, Ni²⁺, Co²⁺); blue = KC1(1 × 10⁻⁵ M)—different metal ions (3000 equiv.) and orange = KC1(1 × 10⁻⁵ M)—Fe³⁺ ion and other metal ions (3000 equiv.) at 585 nm in DMSO:H₂O (7:3 v/v).

Figure 9. FTIR spectra of KC1 (red line) and mixing of KC1+Fe³⁺ ions (black line).

Figure 10. The TLC plates of (a) coated-KC1 (1 × 10⁻³ M) with Fe³⁺ ions in (b) 1 equiv., (c) 5 equiv. and (d) 10 equiv. under a UV lamp at 365 nm in DMSO.

Table 1. Crystal data of KC1.

Compound	Compound KC1
CCDC Number	2361572
Empirical Formula	C30H33NO4S
Formula Weight (g/mol)	503.67
Temperature (K)	296
Wavelength (Å)	0.71073
Crystal System	Triclinic
Space Group	P1
a (Å)	8.7613 (2)
b (Å)	9.6370 (2)
c (Å)	17.5443 (5)
α (◦)	79.447 (1)
β (◦)	84.094 (1)
γ (◦)	66.799 (1)
Volume/Å3	1337.71 (6)
Z	2
Density (calculated) (g/cm³)	1.250
Absorption Coefficient (mm⁻¹)	0.16
F(000)	536.561
Crystal Size (mm³)	0.32 × 0.32 × 0.22
Theta Range for Data Collection (◦)	5 to 57.8
Index Ranges	−11 ≤ h ≤ 11, −13 ≤ k ≤ 13, −23 ≤ l ≤ 23
Reflections Collected	6982
Independent Reflections	5073 [Rint = 0.057]
Max. and Min. Transmission	0.7458 and 0.6903
Data/Restraints/Parameters	5073/0/328
Goodness-of-fit on F2	1.06
Final R Indices [I > 2sigma(I)]	R1 = 0.0457, wR2 = 0.1274
R Indices (all data)	R1 = 0.0706, wR2 = 0.1128
Largest Diff. Peak and Hole	0.26/−0.14 e Å−3

Table 2. Selected bond length (Å) and bond angle (°) of KC1.

Atom-Atom	Bond Length (Å)	Atom-Atom	Bond Length (Å)
S1-O1	1.4195 (14)	S1-C12	1.7614 (15)
C14-C15	1.382 (3)	C16-H16	0.93
S1-O2	1.4235 (14)	O3-C13	1.4124 (18)
C15-H15	0.93	C16-C17	1.380 (3)
S1-O3	1.5992 (12)	O4-C24	1.361 (2)
C15-C16	1.366 (3)	C17-H17	0.93
O4-C25	1.422 (2)	C17-C18	1.394 (2)
N1-C1	1.457 (2)	C18-C19	1.483 (2)
N1-C2	1.449 (2)	C19-C20	1.392 (2)
O2-S1-O1	119.77 (8)	C24-C19-C18	121.14 (14)
C17-C16-C15	120.29 (18)	C3-N1-C2	114.14 (14)
O3-S1-O1	103.49 (8)	C24-C19-C20	118.34 (16)
C17-C16-H16	119.86 (12)	H1a-C1-N1	109.5
O3-S1-O2	109.35 (7)	H20-C20-C19	119.30 (11)
H17-C17-C16	119.14 (12)	H1b-C1-N1	109.5
C12-S1-O1	110.31 (8)	C21-C20-C19	121.4 (2)
C18-C17-C16	121.72 (18)	H1b-C1-H1a	109.5
C12-S1-O2	109.28 (8)	C21-C20-H20	119.30 (13)
C18-C17-H17	119.14 (10)	H1c-C1-N1	109.5
C12-S1-O3	103.25 (6)	H21-C21-C20	120.32 (13)
C17-C18-C13	116.06 (15)	H1c-C1-H1a	109.5
C13-O3-S1	118.79 (9)	C22-C21-C20	119.37 (19)
C19-C18-C13	124.09 (14)	H1c-C1-H1b	109.5
C25-O4-C24	119.31 (14)	C22-C21-H21	120.32 (12)
C19-C18-C17	119.85 (15)	H2a-C2-N1	109.5
C2-N1-C1	110.58 (15)	H22-C22-C21	119.58 (12)
C20-C19-C18	120.31 (16)	H2b-C2-N1	109.5
C3-N1-C1	115.05 (15)	C23-C22-C21	120.84 (19)

Table 3. The main functional groups of KC1 at different wavenumbers.

Wavenumber (cm⁻¹)	Functional Group
2858	-C-H
1095	-C-O
1570 and 1465	-C=C
1152	-C-N
1364 and 1234	-S=O

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Chantaniyomporn, K.; Charoensuk, K.; Duangthongyou, T.; Chainok, K.; Wannalerse, B. A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure. Crystals 2024, 14, 943. https://doi.org/10.3390/cryst14110943

AMA Style

Chantaniyomporn K, Charoensuk K, Duangthongyou T, Chainok K, Wannalerse B. A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure. Crystals. 2024; 14(11):943. https://doi.org/10.3390/cryst14110943

Chicago/Turabian Style

Chantaniyomporn, Kanokporn, Kiratikarn Charoensuk, Tanwawan Duangthongyou, Kittipong Chainok, and Boontana Wannalerse. 2024. "A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure" Crystals 14, no. 11: 943. https://doi.org/10.3390/cryst14110943

APA Style

Chantaniyomporn, K., Charoensuk, K., Duangthongyou, T., Chainok, K., & Wannalerse, B. (2024). A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure. Crystals, 14(11), 943. https://doi.org/10.3390/cryst14110943

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A Fluorescence Sensor Based on Biphenolic Backbone for Metal Ion Detection: Synthesis and Crystal Structure

Abstract

1. Introduction