A New Non-linear Stilbazolium Derivative Crystal of 4-[2-(3 Methoxy-phenyl)-vinyl]-1-methyl-pyridinium+ Iodide− (MMPI): Analysis of Its Structural, Surface, Optical and NLO Properties
Abstract
:1. Introduction
2. Materials and Methods
Material Synthesis, Solubility and Crystal Growth
3. Results & Discussion
3.1. Single Crystal X-ray Diffraction Analysis
3.2. Morphology Studies
3.3. 1H NMR and 13C NMR Studies
3.4. Fourier Transform Infrared Spectroscopy Study
3.5. Linear Absorption Analysis
3.6. Photoluminescence Studies
3.7. Atomic Force Microscopy Study
3.8. Chemical Etching Studies
3.9. SEM Analysis and EDAX Analysis
3.10. Hirshfeld Surface Analysis
3.11. HOMO and LUMO Studies
3.12. MEP Analysis
3.13. Nonlinear Optical Properties by Z-scan Technique
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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CCDC No | 2131739 | |
---|---|---|
Chemical formula | C15H16INO | |
Formula weight | 353.19 g/mol | |
Temperature | 301(2) K | |
Wavelength | 0.71073 Å | |
Crystal size | 0.300 × 0.320 × 0.350 mm | |
Crystal habit | gold block | |
Crystal system | Monoclinic | |
Space group | P 1 21/c 1 | |
Unit cell dimensions | a = 6.8601(6) Å b = 19.7111(16) Å c = 10.8400(8) Å | α = 90° β = 91.207(3)° γ = 90° |
Volume | 1465.5(2) Å3 | |
Z | 4 | |
Density (calculated) | 1.601 g/cm3 | |
Absorption coefficient | 2.174 mm−1 | |
F(000) | 696 | |
Theta range for data collection | 2.07 to 28.30° | |
Index ranges | −9 ≤ h ≤ 9, −26 ≤ k ≤ 26, −14 ≤ l ≤ 14 | |
Reflections collected | 39,250 | |
Independent reflections | 3617 [R(int) = 0.0412] | |
Coverage of independent reflections | 99.4% | |
Absorption correction | Multi-Scan | |
Max. and min. transmission | 0.5620 and 0.5170 | |
Structure solution technique | direct methods | |
Structure solution program | SHELXT 2018/2 [15] | |
Function minimized | Σw(Fo2 − Fc2)2 | |
Data/restraints/parameters | 3617/0/166 | |
Goodness-of-fit on F2 | 1.123 | |
Δ/σmax | 0.001 | |
Final R indices | 2505 data; I > 2σ(I) | R1 = 0.0589, wR2 = 0.1546 |
all data | R1 = 0.0853, wR2 = 0.1715 | |
Weighting scheme | w = 1/[σ2(Fo2) + (0.0632P)2 + 3.5086P] where P = (Fo2 + 2Fc2)/3 | |
Extinction coefficient | 0.0250(30) | |
Largest diff. peak and hole | 0.774 and −0.567 eÅ−3 | |
R.M.S. deviation from mean | 0.144 eÅ−3 |
Bond Lengths (Å) | Bond Angles (°) | ||
---|---|---|---|
Atoms | Length | Atoms | Angle |
O1-C10 | 1.359(7) | C10-O1-C15 | 118.1(5) |
N1-C3 | 1.331(7) | C3-N1-C14 | 120.5(5) |
N1-C14 | 1.479(7) | C5-C1-C2 | 117.2(5) |
C1-C2 | 1.378(9) | C2-C1-C6 | 125.3(6) |
C2-C3 | 1.377(9) | N1-C3-C2 | 119.3(5) |
C6-C7 | 1.295(9) | C4-C5-C1 | 119.9(5) |
C8-C13 | 1.361(8) | C6-C7-C8 | 125.0(6) |
C9-C10 | 1.380(8) | C13-C8-C7 | 115.8(6) |
C11-C12 | 1.362(9) | C10-C9-C8 | 119.5(5) |
O1-C15 | 1.437(9) | O1-C10-C11 | 114.8(5) |
N1-C4 | 1.345(7) | C12-C11-C10 | 120.0(6) |
C1-C5 | 1.378(9) | C8-C13-C12 | 120.6(6) |
C1-C6 | 1.487(8) | C3-N1-C4 | 120.3(5) |
C4-C5 | 1.358(8) | C4-N1-C14 | 119.2(5) |
C7-C8 | 1.471(9) | C5-C1-C6 | 117.5(5) |
C8-C9 | 1.421(8) | C3-C2-C1 | 121.6(6) |
C10-C11 | 1.394(8) | N1-C4-C5 | 121.7(6) |
C12-C13 | 1.383(9) | C7-C6-C1 | 123.3(6) |
- | - | C13-C8-C9 | 119.4(5) |
- | - | C9-C8-C7 | 124.8(5) |
- | - | O1-C10-C9 | 125.4(5) |
- | - | C9-C10-C11 | 119.8(5) |
- | - | C11-C12-C13 | 120.8(6) |
Number | Atom1 | Atom2 | Atom3 | Atom4 | Torsion |
---|---|---|---|---|---|
1 | C15 | O1 | C10 | C9 | −1.92 |
2 | C15 | O1 | C10 | C11 | 178.44 |
3 | C10 | O1 | C15 | H15A | −169.67 |
4 | C10 | O1 | C15 | H15B | 70.33 |
5 | C10 | O1 | C15 | H15C | −49.67 |
6 | C4 | N1 | C3 | C2 | −0.62 |
7 | C4 | N1 | C3 | H3 | 179.38 |
8 | C14 | N1 | C3 | C2 | 178.93 |
9 | C14 | N1 | C3 | H3 | −1.07 |
10 | C3 | N1 | C4 | H4 | −178.82 |
Chemical Shift (ppm) | Assignment |
---|---|
Δ − 2.5 ppm | DMSO-d6 solvent |
δ − 3.380 ppm | water in DMSO-d6 |
δ − 3.833 ppm | methoxy group (O-CH3) in the aromatic ring |
δ − 4.264 ppm | N-CH3 |
δ − 7.031 and 7.052 ppm | aromatic ring in the methoxy group |
δ −7.322 and 7 339 ppm | CH=CH |
δ − 7.396, 7.416 and 7.435 ppm | one hydrogen atom of the methoxy group |
δ − 7.539, and 7.580 ppm | aromatic ring in the hydrogen atom |
δ − 7.969 and 8.010 ppm | Methoxy group—hydrogen atom |
δ − 8.217, 8.233, 8.862 and 8.878 ppm | (C5H4N) |
δ − 31.16 and 47.44 ppm | Methoxy group—carbon atoms |
δ − 24.06, 145.63 and 152.88 | pyridine ring carbon atoms |
δ − 55.78, 113.26, 116.78, 121.32, 130.66, 137.02, 140.97, 160.18, and 206.95 ppm | vinyl group and aromatic ring carbon atoms |
Wavenumber (cm−1) | Assignment |
---|---|
3010.88 cm−1 and 2835.36 cm−1 | Aromatic C–H stretching and alkyl C–H stretching |
1624.06 cm−1 | CH=CH stretching |
1581.63 and 1517.98 cm−1 | Vinyl group of C–C=C–C stretching |
1432 cm−1 | CH3 bending |
1336.67cm−1 | C–N stretching mode |
1028.06 cm−1 | O–CH3 stretching vibration |
960.55 cm−1 | C–H stretching vibration of the pyridinium ring |
829.39 cm−1 | 1, 4 disubstitution in the aromatic ring |
785.03 cm−1 and 715.59 cm−1 | C–H out-plane bending vibration |
597.93, 557.43, and 507.28 cm−1 | phenyl ring of the C–C–C mode |
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Krishnan, N.; Sivaperuman, K. A New Non-linear Stilbazolium Derivative Crystal of 4-[2-(3 Methoxy-phenyl)-vinyl]-1-methyl-pyridinium+ Iodide− (MMPI): Analysis of Its Structural, Surface, Optical and NLO Properties. Crystals 2023, 13, 138. https://doi.org/10.3390/cryst13010138
Krishnan N, Sivaperuman K. A New Non-linear Stilbazolium Derivative Crystal of 4-[2-(3 Methoxy-phenyl)-vinyl]-1-methyl-pyridinium+ Iodide− (MMPI): Analysis of Its Structural, Surface, Optical and NLO Properties. Crystals. 2023; 13(1):138. https://doi.org/10.3390/cryst13010138
Chicago/Turabian StyleKrishnan, Nandhini, and Kalainathan Sivaperuman. 2023. "A New Non-linear Stilbazolium Derivative Crystal of 4-[2-(3 Methoxy-phenyl)-vinyl]-1-methyl-pyridinium+ Iodide− (MMPI): Analysis of Its Structural, Surface, Optical and NLO Properties" Crystals 13, no. 1: 138. https://doi.org/10.3390/cryst13010138
APA StyleKrishnan, N., & Sivaperuman, K. (2023). A New Non-linear Stilbazolium Derivative Crystal of 4-[2-(3 Methoxy-phenyl)-vinyl]-1-methyl-pyridinium+ Iodide− (MMPI): Analysis of Its Structural, Surface, Optical and NLO Properties. Crystals, 13(1), 138. https://doi.org/10.3390/cryst13010138