Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the 2-Aryl-6,8-dibromo-2,3-dihydrquinolin-4(1H)-ones
2.2. Synthesis of the 4-Alkoxy-2-arylquinolines
2.2.1. Oxidative-aromatization of the 2,3-Dihydroquinolin-4(1H)-ones
2.2.2. Oxidative-cyclization of 1-(2-Amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones
2.3. Suzuki-Miyaura Cross-Coupling of the 2-Aryl-6,8-dibromo-4-methoxyquinolines
2.4. Photophysical Property Studies of Systems 6
2.4.1. UV-Vis Absorption Properties of 4-Methoxyquinoline Derivatives 6
2.4.2. The Fluorescence Properties of 4-Methoxyquinoline Derivatives
3. Experimental
3.1. General
3.2. Typical Procedure for the Synthesis of the 2-Amino-4,6-dibromochalcones 2a–d
3.3. Typical Procedure for the Synthesis of 3a–d
3.4. Typical Procedure for the Aromatization of 3a–d with Iodine in Methanol
3.5. Typical Procedure for the One-pot Cyclization and Aromatization of 2 with Iodine in Methanol
3.6. Typical Procedure for the Suzuki-Miyaura Cross Coupling of 3 with Arylvinylboronic Acids
3.7. Crystal Structure Solution and Refinement
Empirical formula | C15H10Br2FNO |
Formula weight | 399.06 |
Temperature | 173(2) K |
Wavelength | 0.71073 Å |
Crystal system | Monoclinic |
Space group | P2(1)/n |
Unit cell dimensions | a = 13.0752(6) Å α = 90°b = 8.0086(3) Å β = 111.8230(10)°c = 14.3026(6) Å γ = 90° |
Volume | 1390.35(10) Å3 |
Z | 4 |
Density (calculated) | 1.906 Mg/m3 |
Absorption coefficient | 5.835 mm−1 |
F(000) | 776 |
Crystal size | 0.41 × 0.40 × 0.20 mm3 |
Theta range for data collection | 1.80 to 27.99°. |
Index ranges | −17 ≤ h ≤ 17, −10 ≤ k ≤ 10, −18 ≤ l ≤ 16 |
Reflections collected | 17097 |
Independent reflections | 3358 [R(int) = 0.0768] |
Completeness to theta = 27.00° | 99.9% |
Absorption correction | Integration |
Max. and min. transmission | 0.3882 and 0.1983 |
Refinement method | Full-matrix least-squares on F2 |
Data / restraints / parameters | 3358 / 0 / 185 |
Goodness-of-fit on F2 | 0.922 |
Final R indices [I>2sigma(I)] | R1 = 0.0277, wR2 = 0.0561 |
R indices (all data) | R1 = 0.0391, wR2 = 0.0584 |
Largest diff. peak and hole | 0.470 and −0.709 e.Å−3 |
4. Conclusions
Acknowledgments
- Sample Availability: Samples of the compounds are available from the authors.
References and Notes
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Khoza, T.A.; Maluleka, M.M.; Mama, N.; Mphahlele, M.J. Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines. Molecules 2012, 17, 14186-14204. https://doi.org/10.3390/molecules171214186
Khoza TA, Maluleka MM, Mama N, Mphahlele MJ. Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines. Molecules. 2012; 17(12):14186-14204. https://doi.org/10.3390/molecules171214186
Chicago/Turabian StyleKhoza, Tebogo Ankie, Marole Maria Maluleka, Neliswa Mama, and Malose Jack Mphahlele. 2012. "Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines" Molecules 17, no. 12: 14186-14204. https://doi.org/10.3390/molecules171214186