Meso-phenyltetrabenzotriazaporphyrin based double-decker lanthanide(iii) complexes: synthesis, structure, spectral properties and electrochemistry
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Electronic Supporting Information Meso-phenyltetrabenzotriazaporphyrin based double-decker lanthanide(iii) complexes: synthesis, structure, spectral properties and electrochemistry Victor E. Pushkarev,* a,b Valery V. Kalashnikov, a Alexander Yu. Tolbin, a Stanislav A. Trashin, a ataliya E. Borisova, b Victor B. Rybakov, b Larisa G. Tomilova a,b and ikolay S. Zefirov a,b a Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny proezd, Chernogolovka, Moscow Region, RF. Fax: ; pushkarev@org.chem.msu.ru b Department of Chemistry, M.V. Lomonosov Moscow State University, 1 Leninskie Gory, Moscow, RF. Fax: ; tom@org.chem.msu.ru Contents list 1. MALDI-TOF mass spectra of the products of synthesis of 2a S2 2. Proposed dearylation mechanism on an example of complex 3b S3 3. Mass spectrometry data S4 4. Simulated MS patterns S13 5. UV-Vis and IR spectra of 3b, 4b and 8b S16 6. MR data S17 7. CVA and SWVA for complexes 3b and 4b S23 8. Spectroelectrochemistry of compounds 3b and 4b S24 9. Crystallographic data and structure refinement for 3a S25 S1
2 Fig. S1 MALDI-TOF mass spectra of the products of the synthesis of 2a: top reaction time 1h; bottom reaction time 2h; isotopic patterns for the molecular ions are shown in insets. Isotopic distributions for the molecular ions of 2a and its dearylation product by HR-MS mass spectrometry (right). S2
3 O O - Lu - - O 2 O O - Lu - - H - Lu - - AlkCH 2 O - AlkCH 2 OH O O - Lu Lu PhOO - AlkCHO AlkCH 2 OH O O - Lu - O O 2e - - Lu Fig. S2 Proposed dearylation mechanism on an example of complex 3b. S3
4 Fig. S3 MALDI-TOF mass spectrum of 2b (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 2b by HR-MS mass spectrometry (right). S4
5 Fig. S4 MALDI-TOF mass spectrum of 3a (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 3a by HR-MS mass spectrometry (right). S5
6 Fig. S5 MALDI-TOF mass spectrum of 3b (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 3b by HR-MS mass spectrometry (right). S6
7 Fig. S6 MALDI-TOF mass spectrum of 4a (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 4a by HR-MS mass spectrometry (right). S7
8 Fig. S7 MALDI-TOF mass spectrum of 4b (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 4b by HR-MS mass spectrometry (right). S8
9 Fig. S8 MALDI-TOF mass spectrum of 5a (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 5a by HR-MS mass spectrometry (right). S9
10 Fig. S9 MALDI-TOF mass spectrum of 5b (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 5b by HR-MS mass spectrometry (right). S10
11 Fig. S10 MALDI-TOF mass spectrum of 6a (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 6a by HR-MS mass spectrometry (right). S11
12 Fig. S11 MALDI-TOF mass spectrum of 7a (left); isotopic pattern for the molecular ion is shown in inset. Isotopic distribution for the molecular ion of 7a by HR-MS mass spectrometry (right). S12
13 ( Ph TBTAP)EuOAc (2a), C 39 H 21 7 Eu, [M OAc] + (theory ) mass % _ ( Ph TBTAP)LuOAc (2b), C 39 H 21 7 Lu, [M OAc] + (theory ) mass % _ ( Ph TBTAP) 2 Eu (3a), C 78 H Eu, [M] + (theory ) mass % _ ( Ph TBTAP) 2 Lu (3b), C 78 H Lu, [M] + (theory ) mass % _ S13
14 ( Ph TBTAP)EuPc (4a), C 71 H Eu, [M] + (theory ) mass % _ ( Ph TBTAP)LuPc (4b), C 71 H Lu, [M] + (theory ) mass % _ ( Ph TBTAP)Eu( H TBTAP) (5a), C 72 H Eu, [M] + (theory ) mass % _ ( Ph TBTAP)Lu( H TBTAP) (5b), C 72 H Lu, [M H] + (theory ) mass % _ S14
15 ( H TBTAP) 2 Eu (6a), C 66 H Eu, [M] + (theory ) mass % ( Ph TBTAP) 3 Eu 2 (7a), C 117 H Eu 2, [M] + (theory ) mass % _ Fig. S12 Corresponding simulated MS patterns of the molecular ions for complexes 2 7. S15
16 Absorbance / a.u. Absorbance / a.u. 1,0 0,8 3b 4b 8b 0,6 0,4 0,2 0, Wavelength / nm 0,10 0,08 3b 4b 8b 0,06 0,04 0,02 0, Wavelength / nm Fig. S13 UV-Vis and IR spectra of 3b, 4b and 8b in CCl 4. S16
17 Fig. S14 1 H MR spectrum of 3a (aromatic region) in [D 8 ]THF with the addition of sodium metal. S17
18 Fig. S15 1 H 1 H COSY MR spectrum of 3a (aromatic region) in [D 8 ]THF with the addition of sodium metal. S18
19 Fig. S16 1 H MR spectrum of 4a (aromatic region) in [D 8 ]THF with the addition of sodium metal. Fig. S17 1 H MR spectrum of 3b (aromatic region) in [D 6 ]DMSO with the addition of 1 2 vol% 2 H 4 H 2 O; distinct signals of the main anti and minor syn rotamer are marked with circles and triangles respectively; indicates signals from residual solvents. S19
20 Fig. S18 1 H 1 H COSY MR spectrum of 3b (aromatic region) in [D 6 ]DMSO with the addition of 1 2 vol% 2 H 4 H 2 O. S20
21 Fig. S19 1 H MR spectrum of compound 4b (aromatic region) in [D 6 ]DMSO with the addition of 1 2 vol% 2 H 4 H 2 O. S21
22 Fig. S20 1 H 1 H COSY MR spectrum of 4b (aromatic region) in [D 6 ]DMSO with the addition of 1 2 vol% 2 H 4 H 2 O. S22
23 Fig. S21 CVA (scan rate 0.10 V s 1 ) and SWVA for complexes 3b (left) and 4b (right) in DCB containing 0.15M [Bu 4 ][BF 4 ]. S23
24 Fig. S22 UV/Vis spectral changes for 3b and 4b in DCB containing 0.2 M [Bu 4 ][BF 4 ] during controlled-potential oxidation at +0.8 V (A, C) and reduction at 0.4 V (B, D) respectively. S24
25 Table S1 Crystallographic data and structure refinement for 3a. Empirical formula C 78 H Eu F w Crystal system Monoclinic Space group P2 1 /c a/å (6) b/å (2) c/å (7) ( ) 90 ( ) (1) ( ) 90 V (Å 3 ) (4) Z 8 D calc (Mg m 3 ) (mm 1 ) F (000) 5368 Crystal size (mm 3 ) (Å) range for data collection ( ) Index ranges 39 h 36; 16 k 7; 44 l 35 Reflections collected Reflections independent (R int ) (0.0216) Absorption correction Empirical (DIFABS) T min /T max / Refinement method Full-matrix least-squares on F 2 Data/restraints/parameters 23609/1314/1627 Goodness-of-fit on F R 1, wr 2 [I>2σ(I)] , R 1, wr 2 (all data) , max, min (e Å 3 ) 0.547, S25
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