Comptes Rendus Chimie

Hiroki Ohara

Atsushi Kobayashi

Masako Kato

Supporting Information  

Effects of N-heteroaromatic ligands on highly luminescent mononuclear copper(I)-halide complexes

Hiroki Ohara, a Atsushi Kobayashi a, b and Masako Kato* a

aDepartment of Chemistry, Faculty of Science, Hokkaid-o University, North-10 West-8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan
bPrecursory Research for Embryonic Science and Technology (PRESTO), Japan Science and Technology Agency (JST), Honcho 4-1-8, Kawaguchi-shi, Saitama 332-0012, Japan



Contents
Table S1. Energy, oscillator strength and major contribution of calculated transition for1-Cl ……………….….....	2
Figure S1. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 1-Cl. .........	3 
Table S2. Energy, oscillator strength and major contribution of calculated transition for 1-Br ……………….….....	4
Figure S2. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 1-Br……	5
Table S3. Energy, oscillator strength and major contribution of calculated transition for 2-Cl ……………….….....	6
Figure S3. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-Cl.……	7
Table S4. Energy, oscillator strength and major contribution of calculated transition for 2-Br ……………….….....	8
Figure S4. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-Br........	9 
Table S5. Energy, oscillator strength and major contribution of calculated transition for 2-I- ……………….….....	10
Figure S5. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-I-……	11 
Table S6. Energy, oscillator strength and major contribution of calculated transition for 3-Cl ……………….….....	12
Figure S6. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 3-Cl……	13
Table S7. Energy, oscillator strength and major contribution of calculated transition for 3-Br ……………….….....	14
Figure S7. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 3-Br........	　　15 
Figure S8. Schematic molecular orbital diagrams of 1-I, 2-I, and 3-I  ……………………….........	　　16


 Table S1. Energy, oscillator strength and major contribution of calculated transition for 1-Cl
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.9464 (420.81)	0.0022	HOMO->LUMO (70)HOMO-1->LUMO (30)
2	2.9884 (414.89) 	0.0164	HOMO-1->LUMO (71)HOMO->LUMO (29)
3	3.0961 (400.46) 	0.0010	HOMO-2->LUMO (100)
4	3.4721 (357.09 	0.0034	HOMO->LUMO+1 (89)HOMO->LUMO+2 (8)HOMO-1->LUMO+1 (3)
5	3.5031 (353.93) 	0.0028	HOMO-1->LUMO+1 (90)HOMO-1->LUMO+2 (7)HOMO->LUMO+1 (3)
6	3.6227 (342.24) 	0.0012	HOMO->LUMO+2 (92)HOMO->LUMO+1 (8)
7	3.6379 (340.81) 	0.0008	HOMO-2->LUMO+1 (77)HOMO-2->LUMO+2 (17)HOMO-1->LUMO+2 (3)HOMO->LUMO+2 (3)
8	3.6687 (337.96) 	0.0081	HOMO-1->LUMO+2 (85)HOMO-1->LUMO+1 (5)HOMO->LUMO+3 (4)HOMO-2->LUMO+1 (4)HOMO->LUMO+4 (2)
9	3.6954 (335.51) 	0.0088	HOMO->LUMO+3 (90)HOMO-1->LUMO+2 (4)HOMO->LUMO+4 (2)HOMO-3->LUMO (2)
10	3.7182 (333.46) 	0.0022	HOMO-3->LUMO (86)HOMO-4->LUMO (8)HOMO->LUMO+3 (3)HOMO-2->LUMO (3)

 





























Figure S1. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 1-Cl. Molecular structure determined by X-ray crystallographic analysis was used for the calculation.





Table S2. Energy, oscillator strength and major contribution of calculated transition for 1-Br
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.9035 (427.02)	0.0042	HOMO->LUMO (100)
2	2.9992 (413.39) 	0.0061	HOMO-1->LUMO (96)HOMO-2->LUMO (4)
3	3.1100 (398.66) 	0.0043	HOMO-2->LUMO (96)HOMO-1->LUMO (4)
4	3.4584 (358.50) 	0.0086	HOMO->LUMO+1 (96)HOMO->LUMO+2 (4)
5	3.5715 (347.15) 	0.0042	HOMO->LUMO+1 (91)HOMO->LUMO+2 (9)
6	3.5878 (345.57) 	0.0050	HOMO->LUMO+2 (88)HOMO->LUMO+3 (5)HOMO->LUMO+1 (4)HOMO->LUMO+5 (3)
7	3.6602 (338.73) 	0.0061	HOMO->LUMO+3 (82)HOMO->LUMO+4 (15)HOMO->LUMO+2 (3)
8	3.6863 (336.34) 	0.0114	HOMO->LUMO+5 (34)HOMO-1->LUMO+2 (24)HOMO-2->LUMO+1 (22)HOMO-1->LUMO+3 (6)HOMO->LUMO+2 (4)HOMO-2->LUMO+2 (3)HOMO->LUMO+3 (3)HOMO-1->LUMO+1 (2)HOMO-1->LUMO+4 (2)
9	3.6941 (335.62) 	0.0050	HOMO->LUMO+5 (47)HOMO-2->LUMO+1 (22)HOMO->LUMO+4 (18)HOMO-1->LUMO+2 (11)HOMO-2->LUMO+2 (2)
10	3.7139 (333.84) 	0.0022	HOMO-4->LUMO (4)HOMO-2->LUMO+1 (41)HOMO-2->LUMO+2 (6)HOMO-1->LUMO+1 (8)HOMO-1->LUMO+2 (39)HOMO-1->LUMO+3 (2)






























Figure S2. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 1-Br. Molecular structure determined by X-ray crystallographic analysis is used for the calculation.




Table S3. Energy, oscillator strength and major contribution of calculated transition for 2-Cl
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.5760 (481.30)	0.0171	HOMO->LUMO (86)HOMO-1->LUMO (14)
2	2.6594 (466.21) 	0.0087	HOMO-1->LUMO (87)HOMO->LUMO (13)
3	2.7324 (453.75) 	0.0005	HOMO-2->LUMO (100)
4	3.3044 (375.21) 	0.0063	HOMO-2->LUMO+1 (100)
5	3.3246 (372.93) 	0.0021	HOMO-4->LUMO (54)HOMO-3->LUMO (46)
6	3.3869 (366.07) 	0.0012	HOMO-1->LUMO+1 (100)
7	3.4218 (362.34) 	0.0336	HOMO-3 ->LUMO (54)HOMO-4->LUMO (46)
8	3.4874 (355.52) 	0.0021	HOMO-2->LUMO+1 (100)
9	3.6433 (340.31) 	0.0110	HOMO->LUMO+2 (100)
10	3.7222 (333.09) 	0.0044	HOMO-1->LUMO+3 (100)

 




























Figure S3. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-Cl. Molecular structure is determined by X-ray crystallographic analysis.




Table S4. Energy, oscillator strength and major contribution of calculated transition for 2-Br
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.4003 (516.53)	0.0015	HOMO->LUMO (100)
2	2.4684 (502.30) 	0.0006	HOMO-1->LUMO (100)
3	2.6196 (473.30) 	0.0065	HOMO-2->LUMO (100)
4	3.1632 (391.96) 	0.0039	HOMO-2->LUMO+1 (100)
5	3.2023 (387.17) 	0.0019	HOMO-3->LUMO (53)HOMO-4->LUMO (25)HOMO-1->LUMO+1 (22)
6	3.2434 (382.27) 	0.0012	HOMO-1->LUMO+1 (64)HOMO-4->LUMO (19)HOMO-3->LUMO (18)
7	3.3502 (370.08) 	0.0241	HOMO-4->LUMO (56)HOMO-3->LUMO (29)HOMO-2->LUMO+1 (15)
8	3.3873 (366.03) 	0.0042	HOMO-2->LUMO+1 (83)HOMO-4->LUMO (17)
9	3.4813 (356.15) 	0.0202	HOMO->LUMO+2 (100)
10	3.5567 (348.59) 	0.0031	HOMO->LUMO+3 (82)HOMO-1->LUMO+2 (18)

 
































Figure S4. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-Br. Molecular structure is determined by X-ray crystallographic analysis.


Table S5. Energy, oscillator strength and major contribution of calculated transition for 2-I-
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.2159 (559.53)	0.0005	HOMO->LUMO (100)
2	2.3137 (535.87) 	0.0009	HOMO-1->LUMO (100)
3	2.4864 (498.65) 	0.0086	HOMO-2->LUMO (100)
4	3.0340 (408.65) 	0.0031	HOMO->LUMO+1 (100)
5	3.1257 (396.66) 	0.0018	HOMO-1->LUMO+1 (56)HOMO-3->LUMO (28)HOMO-4->LUMO (16)
6	3.1589 (392.50) 	0.0017	HOMO-1->LUMO+1 (56)HOMO-3->LUMO (28)HOMO-4->LUMO (16)
7	3.2740 (378.69) 	0.0184	HOMO-4->LUMO (43)HOMO-3->LUMO (31)HOMO->LUMO+2 (26)
8	3.2944 (376.35) 	0.0183	HOMO-3->LUMO (48)HOMO-4->LUMO (25)HOMO-2->LUMO+1 (15)HOMO->LUMO+2 (12)
9	3.3075 (374.86) 	0.0090	HOMO-2->LUMO+1 (55)HOMO->LUMO+2 (21)HOMO-4->LUMO (14)HOMO-3->LUMO (10)
10	3.3713 (367.77) 	0.0025	HOMO->LUMO+3 (100)

 






























Figure S5. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 2-I-. Molecular structure is determined by X-ray crystallographic analysis.
Table S6. Energy, oscillator strength and major contribution of calculated transition for 3-Cl
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.1883 (566.57)	0.0045	HOMO->LUMO (100)
2	2.2480 (551.52) 	0.0027	HOMO-1->LUMO (100)
3	2.4011 (516.36) 	0.0046	HOMO-2->LUMO (100)
4	3.0060 (412.46) 	0.0013	HOMO-3->LUMO (74)HOMO-4->LUMO (26)
5	3.1047 (399.34) 	0.0038	HOMO-1->LUMO+1 (100)
6	3.1270 (396.49) 	0.0143	HOMO-4->LUMO (58)HOMO-1->LUMO (22)HOMO-3->LUMO+1 (20)
7	3.1875 (388.97) 	0.0162	HOMO-1 ->LUMO+1 (59)HOMO-4->LUMO (19)HOMO-3->LUMO (11)HOMO-2->LUMO+1 (11)
8	3.3228 (373.14) 	0.0017	HOMO-2->LUMO+1 (85)HOMO-1->LUMO+1 (15)
9	3.5897 (345.39) 	0.0248	HOMO->LUMO+2 (83)HOMO-1->LUMO+2 (17)
10	3.6775 (337.14) 	0.0006	HOMO-1->LUMO+2 (57)HOMO->LUMO+3 (30)HOMO->LUMO+2 (13)

 






























Figure S6. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 3-Cl. Molecular structure is determined by X-ray crystallographic analysis.



Table S7. Energy, oscillator strength and major contribution of calculated transition for 3-Br
Excited state	Energy / eV (nm)	Oscillator strength 	Major contribution (%)
1	2.0325 (610.00)	0.0016	HOMO->LUMO (100)
2	2.1136 (586.60) 	0.0005	HOMO-1->LUMO (100)
3	2.2736 (545.33) 	0.0055	HOMO-2->LUMO (100)
4	2.8848 (429.79) 	0.0008	HOMO-3->LUMO (57)HOMO-4->LUMO (43)
5	2.9467 (420.75) 	0.0037	HOMO->LUMO+1 (100)
6	2.9941 (414.10) 	0.0165	HOMO-4->LUMO (47)HOMO-3->LUMO (34)HOMO-1->LUMO+1 (19)
7	3.0436 (407.36) 	0.0143	HOMO-1->LUMO+1 (68)HOMO-3->LUMO (19)HOMO-4->LUMO (13)
8	3.1858 (389.18) 	0.0018	HOMO-2->LUMO+1 (100)
9	3.4596 (358.38) 	0.0198	HOMO->LUMO+2 (100)
10	3.5567 (348.59) 	0.0031	HOMO-1->LUMO+2 (55)HOMO->LUMO+3 (35)HOMO->LUMO+2 (10)

 
































Figure S7. Schematic molecular orbital diagrams and orbital shapes related to calculated transition of 3-Br. Molecular structure is determined by X-ray crystallographic analysis.


TD-DFT Calculations 
The electron density in the highest and second highest occupied molecular orbitals (HOMO and HOMO-1) is distributed over the Cu and halogen atoms, while that in the lowest unoccupied molecular orbitals (LUMO) are localized on the L ligand. For complexes 1-Br, 1-I, 2-Br, 2-I, 3-Cl, 3-Br, and 3-I, the HOMO-LUMO transition contributes to the lowest excited state by 100%. For complexes 1-Cl and 2-Cl, the HOMO-LUMO and HOMO-1 to LUMO transitions contribute to the lowest excited state by 61% asnd 39% for 1-Cl, and 86% and 14% for 2-Cl, respectively. Thus, the lowest excited states of complexes 1-X, 2-X, and 3-X are a combination of MLCT and halide-to-ligand charge transfer (XLCT) states ((M+X)LCT). As shown in Figure S8, the HOMO energies of 1-I, 2-I, and 3-I are almost the same, and independent of the L ligands. However, the LUMO energies of 1-I, 2-I, and 3-I are strongly dependent on the * energy level of the L ligands, which suggests the energy of the (M+X)LCT state is controlled by the L ligands.




Figure S8. Schematic molecular orbital diagrams of 1-I, 2-I, and 3-I.




PAGE  



14





Effects of <i>N</i>-heteroaromatic ligands on highly luminescent mononuclear copper(I)–halide complexes

Editorial Board - French

Youngwon Kim

Soonheum Park

Dimeric and monomeric palladium(II) parent-amido (NH<sub>2</sub>) complexes: Synthesis, characterization, and reactivity

Kazem D. Safa

Maryam Allahvirdinesbat

Hassan Namazi

Parvaneh Nakhostin Panahi

Synthesis of organosilyl compounds-containing 1,2,4,5-tetraaryl imidazoles sonocatalyzed by M/SAPO-34 (M: Fe, Co, Mn, and Cu) nanostructures
Kazem D. Safaa,*, Maryam Allahvirdinesbata, Hassan Namazib, Parvaneh Nakhostin Panahic
aOrganosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, Tabriz, 5166614766, Iran
bLaboratory of Dendrimers and Nano-Biopolymers, Faculty of Chemistry, University of Tabriz, Tabriz, 5166614766, Iran
cDepartment of Chemistry, Faculty of Science, University of Zanjan, Iran
Tel: +98 (0)41 33393124 Fax: +98 (0)41 3334 0191
Corresponding author, e-mail: dsafa@tabrizu.ac.ir





































Fig. S1. 1H NMR spectrum of 1-(4-fluorophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1d) in CDCl3

Fig. S2. 13C NMR spectrum of 1-(4-fluorophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1d) in CDCl3




Fig. S3. 1H NMR spectrum of 2-(4-Chlorophenyl)-4,5-diphenyl-1-p-tolyl-1H-imidazole (1e) in CDCl3

Fig. S4. 13C NMR spectrum of 2-(4-Chlorophenyl)-4,5-diphenyl-1-p-tolyl-1H-imidazole (1e) in CDCl3












Fig. S5. 1H NMR spectrum of 1-(3-chlorophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1d) in CDCl3

Fig. S6. 13C NMR spectrum of 1-(3-chlorophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1g) in CDCl3






Fig. S7. 1H NMR spectrum of 4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenol (1h) in DMSO-d6 

Fig. S8. 13C NMR spectrum of 4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenol (1h) in DMSO-d6 









Fig. S9. 1H NMR spectrum of 4,4'-(4,5-diphenyl-1H-imidazole-1,2-diyl)diphenol (1i) in DMSO-d6

Fig. S10. 13C NMR spectrum of 4,4'-(4,5-diphenyl-1H-imidazole-1,2-diyl)diphenol (1i) in DMSO-d6






Fig. S11. 1H NMR spectrum of 4-(2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl)phenol (1j) in DMSO-d6


Fig. S12. 13C NMR spectrum of 4-(2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl)phenol (1j) in DMSO-d6






Fig. S13. 1H NMR spectrum of 1-(4-bromophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1l) in CDCl3

Fig. S14. 13C NMR spectrum of 1-(4-bromophenyl)-4,5-diphenyl-2-p-tolyl-1H-imidazole (1l) in CDCl3











Fig. S15. 1H NMR spectrum of 4,5-diphenyl-2-(thiophen-2-yl)-1-p-tolyl-1H-imidazole (1o) in CDCl3


Fig. S16. 13C NMR spectrum of 4,5-diphenyl-2-(thiophen-2-yl)-1-p-tolyl-1H-imidazole (1o) in CDCl3






Fig. S17. 1H NMR spectrum of 1-benzyl-4,5-diphenyl-2-p-tolyl-1H-imidazole (1p) in CDCl3


Fig. S18. 13C NMR spectrum of 1-benzyl-4,5-diphenyl-2-p-tolyl-1H-imidazole (1p) in CDCl3

Fig. S19. 1H NMR spectrum of 2-(4-((dimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (2b) in CDCl3


Fig. S20. 13C NMR spectrum of 2-(4-((dimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (2b) in CDCl3





Fig. S21. 1H NMR spectrum of 2-(4-((trimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (3b) in CDCl3

Fig. S22. 13C NMR spectrum of 2-(4-((trimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (3b) in CDCl3
 











Fig. S23. 1H NMR spectrum of 2-(4-((triethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (4b) in CDCl3


Fig. S24. 13C NMR spectrum of 2-(4-((triethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (4b) in CDCl3









Fig. S25. 1H NMR spectrum of 2-(4-((triphenylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (5b) in CDCl3


Fig. S26. 13C NMR spectrum of 2-(4-((triphenylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (5b) in CDCl3






 
Fig. S27. 1H NMR spectrum of 2-(4-((methoxydimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (6b) in CDCl3


Fig. S28. 13C NMR spectrum of 2-(4-((methoxydimethylsilyl)methyl)phenyl)-1,4,5-triphenyl-1H-imidazole (6b) in CDCl3











Fig. S29. The XRD patterns of Cu-SAPO-34 (5%)




Fig. S30. TEM image of H-SAPO-34 











Fig. S31. TEM image of H-SAPO-34




Fig. S32. TEM image of Cu-SAPO-34 (5%)



Synthesis of organosilyl compounds-containing 1,2,4,5-tetraaryl imidazoles sonocatalyzed by M/SAPO-34 (M = Fe, Co, Mn, and Cu) nanostructures

Saeed Khodabakhshi

Bahador Karami

Khalil Eskandari

Seyed Jafar Hoseini

Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins

Samad Khaksar

Hanieh Radpeyma

Pentafluorophenylammonium triflate: A highly efficient catalyst for the synthesis of quinoxaline derivatives in water

Alois Fürstner

Quelques commentaires sur la catalyse : la recherche fondamentale précède les applications

Élise Champeil

Anne-Marie Sapse

Synthesis of a mitomycin C–lexitropsin hybrid

Mohammad Ali Zolfigol

Ahmad Reza Moosavi-Zare

Mahmoud Zarei

Supplementary data 
Friedel-Crafts alkylation of 4-hydroxycoumarin catalyzed by sulfonic acid functionalized pyridinium chloride as new ionic liquid
Mohammad Ali Zolfigol*,a, Ahmad Reza Moosavi-Zare*,b and Mahmoud Zareia 
aFaculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.
 bDepartment of Chemistry, University of Sayyed Jamaleddin Asadabadi,








Table of Contents
Data of compounds………………………………………..………………………………...……….............2
NMR spectra of compounds………………………………………………….……………………...............5








Selected Data of Compounds:
3,3'-((4-chlorophenyl)methylene)bis(4-hydroxy-2H-chromen-2-one) (2)


White powder; Mp 259-261 oC; IR (KBr) (υmax, cm-1): 3367, 1608, 1552, 1346, 1240, 762; 1H NMR (400 MHz, DMSO-d6): δ= 6.04 (s,1H), 7.26-7.42 (m, 6H), 7.55-7.69 (m, 2H), 7.87 (d, J = 1.2 Hz, 2H), 8.08 (d, J = 8.8 Hz, 2H), 12.67 (s, 2H, OH); 13C NMR (100 MHz, DMSO-d6): 37.1, 103.6, 116.2, 119.2, 123.6, 123.8, 124.5, 128.4, 132.1, 145.9, 150.8, 152.8, 164.8, 167.1.
4-(bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzonitrile (3)


White powder; Mp: 260-262 oC; IR (KBr) (υmax, cm-1): 3369, 2298, 1691.3, 1606.4, 1286.3; 
1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.60 (s, 1H), 7.32-7.33 (m, 4H), 7.52-7.47 (m, 2H), 7.66-7.59 (m, 2H), 7.83-7.80 (m, 2H) 7.95-7.95, (m, 2H), 12.65 (s, 2H, OH); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 37.0, 91.4, 116.2, 116.8, 123.6, 124.3, 129.0, 129.7, 131.1, 133.1, 133.3, 153.9, 162.3, 166.1, 167.7.



3,3'-(pyridin-4-ylmethylene)bis(4-hydroxy-2H-chromen-2-one) (6)

White powder; Mp: 270-274 ˚C; 1H NMR (400 MHz, DMSO-d6/D2O): δ= 6.38 (s, 1H), 7.19-7.26 (m, 4H), 7.45-7.51 (m, 2H), 7.73-7.75 (m, 4H), 8.6-8.58 (d, J= 8 Hz, 2H); 13C NMR (100 MHz, DMSO-d6/D2O): 37.7, 101.3, 115.7, 119.3, 123.1, 124.1, 125.1, 131.5, 140.9, 162.6, 164.0, 164.7, 168.0.

3,3'-(thiophen-2-ylmethylene)bis(4-hydroxy-2H-chromen-2-one) (7)

White powder; Mp: 197-201˚C; 1H NMR (400 MHz, DMSO-d6/D2O): 6.43 (s, 1H), 6.63 (d, J= 0.8 Hz, 1H), 6.81 (t, J= 4 Hz, 1H), 7.18 (d, J= 4.8 Hz, 1H), 7.25-7.30 (m, 4H), 7.54 (t, J= 7.2 Hz, 2H), 7.86 (d, J= 6.8 Hz, 2H); 13C NMR (100 MHz, DMSO-d6/D2O): δ (ppm) 33.2, 104.3, 116.1, 119.6, 123.4, 123.71, 123.79, 124.6, 126.7, 131.9, 147.5, 152.8, 164.6, 167.5.






3,3',3'',3'''-(1,4-phenylenebis(methanetriyl))tetrakis(4-hydroxy-2H-chromen-2-one) (10)




White powder; Mp: 312-314 ˚C; 1H NMR (400 MHz, DMSO-d6/D2O): δ (ppm) 6.01 (s, 2H), 6.83 (s, 4H), 7.16-7.21 (m, 8H), 7.47-7.43 (m, 4H), 7.78 (d, J= 7.6 Hz, 4H); 13C NMR (100 MHz, DMSO-d6/D2O): δ (ppm) 39.1, 103.6, 104.3, 113.3, 116.1, 119.2, 120.1, 123.7, 124.4, 125.7, 127.9, 129.9, 131.8, 138.0, 148.9, 152.7, 165.1, 166.6, 168.1, 185.5, 193.2.









3,3'-((4-chlorophenyl)methylene)bis(4-hydroxy-2H-chromen-2-one) (2)



4-(bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzonitrile (3)


3,3'-(pyridin-4-ylmethylene)bis(4-hydroxy-2H-chromen-2-one) (6)





3,3'-(thiophen-2-ylmethylene)bis(4-hydroxy-2H-chromen-2-one) (7) 



3,3',3'',3'''-(1,4-phenylenebis(methanetriyl))tetrakis(4-hydroxy-2H-chromen-2-one) (10) 


1


Friedel–Crafts alkylation of 4-hydroxycoumarin catalyzed by sulfonic-acid-functionalized pyridinium chloride as a new ionic liquid

Mohammad Reza Poor Heravi

Shadi Mehranfar

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One-pot multicomponent synthesis hexahydroquinoline derivatives in Triton X-100 aqueous micellar media

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Editorial Board - French

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Friedel–Crafts alkylation of 4-hydroxycoumarin catalyzed by sulfonic-acid-functionalized pyridinium chloride as a new ionic liquid

One-pot multicomponent synthesis hexahydroquinoline derivatives in Triton X-100 aqueous micellar media

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