Supporting Information

Μέγεθος: px

Εμφάνιση ξεκινά από τη σελίδα:

Download "Supporting Information"

Ζεφύρα Αγγελόπουλος
6 χρόνια πριν
Προβολές:

1 Supporting Information Wiley-VC Weinheim, Germany

2 ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas Zumbusch, Prof. Dr. Ewald Daltrozzo* Experimental Section General Solvents were purified according to standard procedures. Column chromatography was performed on Merck silica gel 0 (-00 Ñm, 70-0 mesh ASTM). MR spectra were recorded on a Jeol JM-GX-00 (00 Mz) spectrometer. The residual solvent peak was used as internal reference [CCl δ = 7.. C DCl δ =.98]. Multiplicity (singlet (s), broad (br), doublet (d), triplet (t), quartet (q) and multiplet (m)) and coupling constant(s) were reported whenever possible. MALDI-TF mass spectra were recorded on a Bruker Biflex III instrument in positive linear mode.,-dihydroxybenzoic acid (DB) was used as matrix. Elemental analyses were performed in the microanalytical lab of University of Konstanz with an C-analyser Vario EL from Elementar. Absorption and emission were recorded at ambient temperature ( ± C) using quartz -cm cuvettes ( ml). UV/Vis/IR absorption were recorded on a Varian spectrometer, Model Cary 0 and on a Perkin Elmer spectrometer, Model Lambda 9. Fluorescence was recorded at a self assembled IR fluorescence spectrometer with a nitrogen cooled germanium diode (orthcoast) as detector. For exitation a diode laser (80 nm, 0 mw, Laser 000 Model ACM0/7) or a e-e laser (.8 nm, mw, Spectra-Physics model 0-) were used. CZ (Φ F = 0,0 in C Cl at ambient temperature) was used as reference to determine the quantum yields. [7]

3 Purification and physical data of IR dyes b-h IR dye b C 8 7 ' ' 7' ' S ' ' ' C C S 7 C 8 Column chromatography (CCl ) yielded b in 9% as a green crystal powder. -MR (00 Mz, CDCl ): δ/ppm =. (s, ; -), 7.9 (d, J = 8. z, ; - ), 7. (m, ; AA ), 7.9 (d, J =.7 z, ; -7 ), 7. (dd, J = 8. z, J =.7 z, ; - ) 7.0 (m, ; XX ),.0 (t, J =. z, ; -C ),.8 (m, ; -C -C ),. (m, ; -C -C -C ),.8 (s, 8 ; tert-butyl),.9-. (br, ; alkyl), 0.9 (t, ; C ); MALDI-MS: m/z calcd: 99. [M+] +, found 98.7; UV/Vis/IR (CCl ): ν 00 = 00 cm (λ 00 = 7 nm); ǫ 00 = 000 M cm ; f = 0.7; elemental analysis calcd (%) for C 0 8 S [M = 99. g/mol]: C ; found: C IR dye c C 8 7 ' ' ' ' C ' ' C 7 C 8 Column chromatography (CCl ) yielded c in 7% as a green crystal powder. -MR (00 Mz, CDCl ): δ/ppm =.9 (s, ; -), 8. (s, ; - ), 7.9 (d, J = 7.8 z, ; -8 ), 7.79 (d, J = 8.0 z, ; - ), 7.7 (m, ; -,AA ), 7. (m, ; -7 ), 7. (d, ; XX ),.0 (t, J =. z, ; -C ),.87 (m, ; -C -C ),. (m, ; -C -C -C ),.-.7 (m, ; alkyl), 0.9 (t, ;

4 C ); MALDI-MS: m/z calcd: 87. [M+] +, found 87.8; UV/Vis/IR (CCl ): ν 00 = 0 cm (λ 00 = 7 nm); ǫ 00 = 000 M cm ; f = 0.7; elemental analysis calcd (%) for C 8 [M = 87.0 g/mol]: C 7.7..; found: C IR dye d ' ' ' ' ' ' C C 8 7 C C 8 7 Column chromatography (CCl ) yielded d in % as a green-blue crystal powder. -MR (00 Mz, C D Cl ): δ/ppm =. (s, ; -), 7.7 (d, ; AA ), 7.8 (dd, ; - ), 7. (d, ; - ), 7.0 (d, ; XX ),.89 (d, ; - ),.0 (t, J =. z, ; -C ),. (s, ; C ),.8 (m, ; -C -C ),.7 (m, ; -C -C -C ),.-. (br, ; alkyl), 0.89 (t, ; C ); MALDI-MS: m/z calcd: 77. [M+] +, found 77.; UV/Vis/IR (CCl ): ν 00 = 70 cm (λ 00 = 70 nm); ǫ 00 = M cm ; f = 0.8 IR dye e ' ' ' ' C ' ' C Column chromatography (CCl ) yielded e in % as a green crystal powder. -MR (00 Mz, C D Cl ): δ/ppm =.8 (s, ; -), 8.0 (d, ; - ), (br, 0 ; AA,-,7,8 ), 7. (d, ; - ), 7. (d, ; XX ),.97 (s, ; C ),. (s, 8 ; tert-butyl); MALDI-MS: m/z calcd: 7. [M+] +, found 7.;

5 UV/Vis/IR (CCl ): ν 00 = 90 cm (λ 00 = 70 nm); ǫ 00 = 000 M cm ; f = 0.8 IR dye f C 9 ' ' ' ' C ' ' C 9 C Column chromatography (CCl ) yielded f in 7% as a green crystal powder. -MR (00 Mz, CDCl ): δ/ppm =. (br, ; -), 8.0 (d, J = 8.9 z, ; - ), 7.77 (m, 8 ; AA,-7,-8 ), 7.7 (d, J = 8.9 z, ; - ), 7. (s, ; - ), 7. (d, ; XX ),.08 (t, J =. z, ; -C ),.8 (m, ; -C - C ),. (m, ; C -C ),. (s, 8 ; tert-butyl),.0 (t, J = 7. z, ; C ); MALDI-MS: m/z calcd: 8. [M+] +, found 8.; UV/Vis/IR (CCl ): ν 00 = 80 cm (λ 00 = 7 nm); ǫ 00 = 0000 M cm ; f = 0. IR dye g (C ) ' ' ' ' C ' ' C (C ) Column chromatography (CCl ) yielded g in % as a green crystal powder. -MR (00 Mz, C D Cl ): δ/ppm =.8 (s, ; -), 8.07 (d, J = 8.8 z, ; - ), 7.79 (m, 8 ; AA,-7,-8 ), 7.7 (d, J = 8.8 z, ; - ) 7.7 (d, J =.7 z, ; - ), 7. (d, ; XX ),.90 (m, ; C -C-C ),.0 (m, ; C-C ),. (t, J =. z, ; -C ),.8 (m, ; C -C-C ),.88 (m, ;

6 -C -C ),. (m, ; -C -C -C ),. (s, 8 ; tert-butyl); MALDI- MS: m/z calcd: 897. [M+] +, found 897.; UV/Vis/IR (CCl ): ν 00 = 80 cm (λ 00 = 7 nm); ǫ 00 = 000 M cm ; f = 0.9; IR dye h By drying the organic phase over MgS the violett product adsorbed at the MgS. The solvent was refused from the filtrate and the blue : condensation product h was yielded by column chromatography (CCl /Me 0/) in %. The MgS was dissolved in water and the violet solid was filtered off. It was washed in water and digested with aceton in the ultrasonic bath. The solid was filtered of and washed with acetone. This procedure was repeated until the washing liquid was clear and yielded h in 8%. Physical data of IR dye h C 8 7 ' ' ' ' C ' ' ' C 7 C 8 -MR (00 Mz, C D Cl ): δ/ppm =.78 (s, ; -), 8.0 (d, J = 8. z, ; - ), 7.8 (m, 0 ; AA,-,-7,-8 ), 7.7 (s, ; - ),.9 (d, ; XX ),. (br, ; -C ),. (s, ; -C ),.9 (m, ; -C C ),.8-. (m, 8 ; alkyl, tert-butyl), 0.88 (t, ; C ); MALDI-MS: m/z calcd: 98. [M+] +, found 98.9; UV/Vis/IR (CCl ): ν 00 = 00 cm (λ 00 = 7 nm); ǫ 00 = 000 M cm ; f = 0.

7 Physical data of IR dye h C 8 7 ' ' ' ' C ' ' '' '' '' '' 7 C 8 '' '' -MR (00 Mz, C D Cl ): δ/ppm =.8 (s, ; - ), d (8., ; AA ), 8.0 (m, ; -7 ), 7.9 (d, ; - ), 7.8 (d, ; - ), 7.7 (m, ; -8 ), 7. (s, ; -), 7. (d, ; (AA ) ),.8 (d, ; XX ),.79 (m, ; (XX ) ),.7 (m, ; - ),. (br, ; -C ),.09 (s, ; -C ),.0 (s, ; -C ),. (m, ; -C C ),. (s, 9 ; tert-butyl),.-. (br, 0 ; alkyl), 0.88 (m, ; C ); MALDI-MS: m/z calcd: 778. [M+] +, found 777.9; UV/Vis/IR (C Cl ): ν 00 = 0 cm (λ 00 = 9 nm)

Σχετικά έγγραφα

A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes