supporting information for356 mv[sum= 13885 mv] profiles 1-39 smooth av 20 -baseline 80 reflectron...
TRANSCRIPT
Supporting Information for:
Synthesis and photophysical properties of phosphorus (V)
porphyrins functionalized with axial carbazolylvinylnaphthalimides
Yong Zhan,a Kaiyu Cao,a Chenguang Wang,a Junhui Jia,a Pengchong Xue,a Xingliang Liu,a Xuemei Duan,b Ran Lu a,*
a State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, P. R. China.
b State Key Laboratory of Theoretical and Computational Chemistry, Institute of
Theoretical Chemistry, Jilin University, Changchun 130021, P. R. China.
Fax: +86-431-88923907; Tel: +86-431-88499179
E-Mail: [email protected]
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Table S1. Photophysical data of phosphorus (V) porphyrins 1, 2 and 12. Absorption (λmax/nm) (ε×10-4/M-1 cm-1)a Emission(nm)b
Compound Soret Q1 Q2
1 300 (7.51) 350 (5.05) 440 (26.25) 564 (1.94) 611(1.00) 620, 672
2 300 (7.69) 350 (8.20) 440 (16.60) 564 (1.40) 610 (0.64) 620, 672
12 300 (0.44) 350 (0.35) 437 (5.71) 563 (0.45) 606 (0.34) 618, 669 a measured in CHCl3 (1.0×10-6 M) at room temperature. b measured in CHCl3 (1.0×10-6 M) at room temperature, excited at 570 nm.
Fig. S1 Normalized (a) UV-vis absorption and (b) Fluorescence emission spectra of compound 8 in different solvents (1.0 × 10-6 M, ex = 440 nm).
Fig. S2 Normalized UV-vis absorption of (a) phosphorus (V) porphyrins 1 and 12 (5.0 × 10-6 M), and compound 8 (1.0 × 10-5 M) in chloroform; (b) phosphorus (V) porphyrins 2 and 12 (5.0 × 10-6 M), and compound 9 (1.0 × 10-5 M) in chloroform.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S3 Normalized UV-vis absorption spectra of phosphorus (V) porphyrins 1 and 2 in the film.
Fig. S4 Cyclic voltammogram diagrams of phosphorus (V) porphyrins 1 and 2 in anhydrous CH2Cl2 with 0.1 M Bu4NBF4 as electrolyte at a scan rate of 100 mV s-1.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
CHO
Fig. S5 1H-NMR (300 MHz, CDCl3) spectrum of compound 3.
N
CHO
Fig. S6 MALDI/TOF MS spectrum of compound 3.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
CHOI
Fig. S7 1H-NMR (300 MHz, CDCl3) spectrum of compound 4.
N
CHOI
Fig. S8 MALDI/TOF MS spectrum of compound 4.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
CHO
N
Fig. S9 1H-NMR (500 MHz, CDCl3) spectrum of compound 6.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
200 300 400 500 600 700 800 900 1000Mass/Charge
173 mV[sum= 3106 mV] Profiles 24-41 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR-216-L0001.L18 14 Oct 2011 11:36 Cal: 31 Oct 2011 19:16 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 40, P.Ext. @ 610 (bin 57)
610.8
N
N
CHO
Fig. S10 MALDI/TOF MS spectrum of compound 6.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
N
Fig. S11 1H-NMR (500 MHz, CDCl3) spectrum of compound 7.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
100 200 300 400 500 600 700 800 900 1000Mass/Charge
356 mV[sum= 13885 mV] Profiles 1-39 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR169-L0001.H7 31 May 2011 10:05 Cal: 2 Jan 2002 16:12 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 90, P.Ext. @ 608 (bin 57)
608.5
N
N
Fig. S12 MALDI/TOF MS spectrum of compound 7.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
O
O
OMeNC8H17
Fig. S13 1H-NMR (300 MHz, CDCl3) spectrum of compound 8.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
400 500 600 700 800 900 1000Mass/Charge
432 mV[sum= 9502 mV] Profiles 17-38 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR208-L0001.F17 20 Sep 2011 11:13 Cal: 2 Jan 2002 23:30 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 50, P.Ext. @ 606 (bin 57)
607.6
477.7
464.1
N N
O
O
OMe
Fig. S14 MALDI/TOF MS spectrum of compound 8.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
N
C8H17
C8H17
N
O
O
OMe
Fig. S15 1H-NMR (300 MHz, CDCl3) spectrum of compound 9.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
400 500 600 700 800 900 1000 1100 1200Mass/Charge
458 mV[sum= 10980 mV] Profiles 1-24 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR209-L0001.G17 20 Sep 2011 11:14 Cal: 2 Jan 2002 23:31 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 50, P.Ext. @ 910 (bin 57)
910.8
477.7 636.2
N
N
NO
OOMe
Fig. S16 MALDI/TOF MS spectrum of compound 9.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S17 1H-NMR (300 MHz, CDCl3) spectrum of compound 10.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
500 520 540 560 580 600 620 640 660 680 700 720 740 760 780 800 820 840 860Mass/Charge
155 mV[sum= 2936 mV] Profiles 1-19 Smooth Av 20 -Baseline 80
Reflectron Mode DKr
ata: 2470001.N22 4 Nov 2011 14:56 Cal: 4 Nov 2011 15:18 atos PC Axima CFR V2.3.1: Mode default_linear, Power: 60, P.Ext. @ 592 (bin 57)
593.3
Fig. S18 MALDI/TOF MS spectrum of compound 10.
Fig. S19 1H-NMR (300 MHz, DMSO-d6) spectrum of compound 11.
608.7
N N
O
O
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
0
10
20
30
40
50
60
70
80
90
100
%Int.
700 750 800 850 900 950 1000Mass/Charge
316 mV[sum= 11372 mV] Profiles 44-79 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR133-R0001.J3 29 Apr 2011 10:45 Cal: 18 Jan 2002 7:58 Kratos PC Axima CFR V2.3.1: Mode default_reflectron, Power: 90, P.Ext. @ 896 (bin 82)
896.5
N
N
NO
OOH
Fig. S20 MALDI/TOF MS spectrum of compound 11.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
N
O
O
ON
NN
NP
N
N
O
O
O
Fig. S21 1H-NMR (600 MHz, CDCl3) spectrum of compound 1.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S22 13C-NMR (75 MHz, CDCl3) spectrum of compound 1.
0
10
20
30
40
50
60
70
80
90
100
%Int.
1500 1550 1600 1650 1700 1750 1800 1850 1900 1950 2000Mass/Charge
60 mV[sum= 4998 mV] Profiles 25-108 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR167-L0001.J7 31 May 2011 10:02 Cal: 2 Jan 2002 16:02 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 100, P.Ext. @ 1825 (bin 57)
1827.6
1523.2
N
N
O
O
ON
NN
NP
N
N
O
O
O
Fig. S23 MALDI/TOF MS spectrum of compound 1. Fig. S23 MALDI/TOF MS spectrum of compound 1.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S24 High resolution mass spectrum of compound 1.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
N
N
N
O
O
ON
NN
NP
N
N
N
O
O
O
Fig. S25 1H-NMR (600 MHz, CDCl3) spectrum of compound 2.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S26 13C-NMR (125 MHz, CDCl3) spectrum of compound 2.
0
10
20
30
40
50
60
70
80
90
100
%Int.
2000 2100 2200 2300 2400 2500 2600 2700Mass/Charge
83 mV[sum= 8169 mV] Profiles 34-131 Smooth Av 20 -Baseline 80
Reflectron Mode Data: LR168-L0001.I7 31 May 2011 10:04 Cal: 2 Jan 2002 16:10 Kratos PC Axima CFR V2.3.1: Mode default_linear, Power: 90, P.Ext. @ 2432 (bin 58)
2434.5
2159.1 2450.9
N
N
N
O
O
ON
NN
NP
N
N
N
O
O
O
Fig. S27 MALDI/TOF MS spectrum of compound 2.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
Fig. S28 High resolution mass spectrum of compound 2.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012