SYNTHESIS AND LUMINESCENCE OF. SOLUBLE meso-unsubstituted TETRABENZO- AND TETRANAPHTHO [2,3]PORPHYRINS
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1 S1 SYNTHESIS AND LUMINESCENCE OF SOLUBLE meso-unsubstituted TETRABENZO- AND TETRANAPHTHO [2,3]PORPHYRINS SUPPORTING INFORMATION Olga S. Finikova, a Andrei V. Cheprakov b and Sergei A. Vinogradov a * a Department of Biochemistry and Biophysics, University of Pennsylvania, Philadelphia, PA 19104; b Department of Chemistry, Moscow State University, Moscow , Russia. * To whom correspondence should be addressed. Phone: (215) , FAX: (215) , vinograd@mail.med.upenn.edu
2 S2 Table of Contents Materials and Methods References and Notes NMR spectra S3 S3 S4
3 S3 Materials and Methods All solvents were purified according to the standard procedures. Selecto silica gel or neutral aluminum oxide (Brockmann I, ~150 mesh) was used for column chromatography. All starting materials and reagents were obtained from standard commercial suppliers. Analytical TCL's were run on commercial Riedel-de Haën plates coated with silica gel 60F 264 (0.2-mm thickness). Static fluorescence and phosphorescence measurements were performed on SPEX Fluorolog-2 spectrofluorometer (Jobin-Yvon Horiba, Inc.), equipped with an infra-red enhanced R2658P PMT (Hamamatsu). Phosphorescence lifetimes were measured using an in-house constructed frequency domain phosphorometer. 1 Solutions for phosphorescence measurements were purged with Ar. The absorbances of the samples at the wavelengths used for excitation were kept below 0.05 OD. The quantum yields were obtained by computing the integrals of the corrected emission spectra and referencing them to the fluorescence quantum yield of ZnTPP in deoxygenated benzene (φ fluor =0.033). 2 The spectra were normalized by the optical density of the samples at the excitation wavelengths, relative photon intensity of the source and quantum efficiency of the detector throughout the emission range. Phosphorescence oxygen quenching constants (K q ) were determined as described previously. 3 References and Notes (1) Vinogradov, S. A.; Fernandez-Seara, M. A.; Dugan, B. W.; Wilson, D. F. Rev. Sci. Instrum. 2001, 72, (2) Quimby, D. J.; Longo, F. R. J. Am. Chem. Soc. 1975, 97, (3) Rozhkov, V.V.; Wilson, D.F.; Vinogradov, S.A. Macromolecules 2002, 35, 1991.
4 NMR spectra S4
5 S b, 1H NMR, CDCl PPM STANDARD 1H OBSERVE USER: -- DATE: Dec F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_tbpso2.fid
6 S6 2b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Dec F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 320 LB: 0.0 WinNuts - $of_tbpso2_13c.fid
7 S b, 1H NMR, CDCl PPM STANDARD 1H OBSERVE USER: -- DATE: Dec F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_bupybn.fid
8 S b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Mar F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 2832 LB: 0.0 WinNuts - $of_3b.fid
9 S c, 1H NMR, CDCl PPM STANDARD PROTON PARAMETERS USER: -- DATE: Nov F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 8 LB: 0.0 WinNuts - $of96.fid
10 S c, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Nov F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 128 LB: 0.0 WinNuts - $of96_13c.fid
11 S b, 1H NMR, CDCl MeOH H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Mar F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 5.0 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of105.fid
12 S12 4b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Mar F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 0.0 sec NA: 80 LB: 0.0 WinNuts - $of105_13c.fid
13 S a (mixture of isomers), 1H NMR, CDCl CHCl3 H2O PPM STANDARD PROTON PARAMETERS USER: -- DATE: Feb F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 64 LB: 0.0 WinNuts - $of7.fid
14 S Zn-5a (mixture of isomers), 1H NMR, DMSO-d6 H2O 4.00 DMSO PPM STANDARD PROTON PARAMETERS USER: -- DATE: Oct F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 25 LB: 0.0 WinNuts - $fb_mh4tchpzn_dmso.fid
15 S15 5b (mixture of isomers), 1H NMR, CDCl PPM STANDARD PROTON PARAMETERS USER: -- DATE: May F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 8 LB: 0.0 WinNuts - $of36tchp.fid
16 S16 Zn-5b (mixture of isomers), 1H NMR, DMSO-d H2O 4.00 dmso PPM STANDARD 1H OBSERVE USER: -- DATE: Mar F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_buzn.fid
17 S b, 1H NMR, CDCl CHCl H2O PPM STANDARD PROTON PARAMETERS USER: -- DATE: May F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 100 LB: 0.0 WinNuts - $of40.fid
18 S b (dication form) in TFA-d tfa tfa PPM STANDARD CARBON PARAMETERS USER: -- DATE: Jun F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 7484 LB: 0.0 WinNuts - $of59_13c.fid
19 S19 o Zn-6b, 1H NMR, ridine-d5 (50 C) H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Dec F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.0 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of78_50.fid
20 S o Zn-6b, 13C NMR, ridine-d5 (50 C) PPM STANDARD CARBON PARAMETERS USER: -- DATE: Dec F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $of78_13c.fid
21 S21 o Pd-6b, 1H NMR, ridine-d5 (70 C) H2O PPM STANDARD PROTON PARAMETERS USER: -- DATE: May F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 70 LB: 0.0 WinNuts - $of49_70.fid
22 S o Pd-6b, 13C NMR, ridine-d5 (70 C) PPM STANDARD CARBON PARAMETERS USER: -- DATE: May F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $of49_13c.fid
23 S23 o Pt-6b, 1H NMR, ridine-d5 (80 C) H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Nov F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_pt80.fid
24 S o Pt-6b, 13C NMR, ridine-d5 (70 C) PPM STANDARD CARBON PARAMETERS USER: -- DATE: Dec F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $ofpt_13c.fid
25 S25 Fe-6b, 1H NMR, ridine-d H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Nov F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 100 LB: 0.0 WinNuts - $of_fe.fid
26 S Fe-6b, 13C NMR, ridine-d PPM STANDARD CARBON PARAMETERS USER: -- DATE: Dec F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $of_fe_13c.fid
27 S27 8b, 1H NMR, CDCl PPM STANDARD PROTON PARAMETERS USER: -- DATE: Feb F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 8 LB: 0.0 WinNuts - $of9a.fid
28 S28 8b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Mar F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 256 LB: 0.0 WinNuts - $of_8b.fid
29 S c, 1H NMR, CDCl PPM STANDARD PROTON PARAMETERS USER: -- DATE: Jul F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 8 LB: 0.0 WinNuts - $of70_final.fid
30 S30 8c, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Jul F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 2130 LB: 0.0 WinNuts - $of70_13c.fid
31 S31 9b, 1H NMR, CDCl PPM STANDARD PROTON PARAMETERS USER: -- DATE: Feb F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 8 LB: 0.0 WinNuts - $of12a.fid
32 S b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Mar F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 432 LB: 0.0 WinNuts - $of_9b.fid
33 S c, 1H NMR, CDCl PPM STANDARD 1H OBSERVE USER: -- DATE: Dec F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.7 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_mesocl.fid
34 S c, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Dec F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 896 LB: 0.0 WinNuts - $of74_13c.fid
35 S b, 1H NMR, CDCl3 CHCl H2O PPM STANDARD PROTON PARAMETERS USER: -- DATE: Sep F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 66 LB: 0.0 WinNuts - $of79_1c.fid
36 S b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Sep F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 2302 LB: 0.0 WinNuts - $of79c_13c.fid
37 S b, 1H NMR, CDCl CHCl H2O PPM STANDARD PROTON PARAMETERS USER: -- DATE: Sep F1: F2: SW1: OF1: PTS1d: EX: s2pul PW: 5.5 usec PD: 0.0 sec NA: 66 LB: 0.0 WinNuts - $of80.fid
38 S38 11b, 13C NMR, CDCl PPM STANDARD CARBON PARAMETERS USER: -- DATE: Sep F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: 2050 LB: 0.0 WinNuts - $of80_13c.fid
39 S b, 1H NMR, solvent mixture ridine-d5 - PhNO2-d5 (1:1) 8.29 Py, PhNO PPM STANDARD 1H OBSERVE USER: -- DATE: Apr F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.0 usec PD: 1.0 sec NA: 160 LB: 0.0 WinNuts - $of1i.fid
40 S40 o 13b, 13C NMR, solvent mixture ridine-d5 - PhNO2-d5 (80 C) PPM STANDARD CARBON PARAMETERS USER: -- DATE: Apr F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $of1i_13c.fid
41 S Zn-13b, 1H NMR, ridine-d H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Apr F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.0 usec PD: 1.0 sec NA: 8 LB: 0.0 WinNuts - $of_2i.fid
42 S42 Zn-13b, 13C NMR, ridine-d PPM STANDARD CARBON PARAMETERS USER: -- DATE: Apr F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $of2i_13c.fid
43 S43 o Pd-13b, 1H NMR, ridine-d5 (100 C) H2O PPM STANDARD 1H OBSERVE USER: -- DATE: Jul F1: F2: SW1: 8000 OF1: PTS1d: EX: s2pul PW: 11.0 usec PD: 1.0 sec NA: 64 LB: 0.0 WinNuts - $13bPd_100.fid
44 S44 o Pd-13b, 13C NMR, ridine-d5 (80 C) Because of the aggregation, only side chains carbons' signals are resolved PPM STANDARD CARBON PARAMETERS USER: -- DATE: Jul F1: F2: SW1: OF1: PTS1d: 8192 EX: s2pul PW: 13.0 usec PD: 2.0 sec NA: LB: 0.0 WinNuts - $13bPd_13C.fid
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