Selective bromination of perylene diimides under mild conditions.
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1 SUPPORTING INFORMATION Selective bromination of perylene diimides under mild conditions. Paramasivan Rajasingh, Revital Cohen, Elijah Shirman, Linda J. W. Shimon, and Boris Rybtchinski Department of Organic Chemistry and Chemical Research Support Unit, Weizmann Institute of Science, Rehovot 76100, Israel CONTENTS: General Methods...S2 NMR spectra of 1a and 2a...S3 NMR spectra of 3a and 3b before and after recrystallization...s4 NMR spectra of compounds S6 XYZ coordinates of the calculated structures and transition states...s13 Department of Organic Chemistry Chemical Research Support Unit S1
2 General Methods. Solvents and reagents were obtained from commercial sources and used as received. NMR spectra were recorded at room temperature on 500 MHz NMR spectrometer unless otherwise specified. CDCl 3 was used as an NMR solvent. The chemical shifts (δ) are reported in parts per million (ppm) from tetramethylsilane (TMS, 0.00 ppm). Proton spectra recorded in CDCl 3 were referenced to TMS. Carbon spectra recorded in CDCl 3 were referenced to the peak of CDCl 3 (77.0 ppm). The solvents for spectroscopic studies were of spectroscopic grade and used as received. UV/vis and fluorescence spectra were measured on standard instruments and fluorescence quantum yields were determined using N,N -Bis(2,4-dimethylpent- 3-yl)perylene-3,4:9,10-tetracarboxylicdiimide (Ф = 1) as reference for compounds 2a, 2b, 3a, 3b, 5a and 5b and N,N -Dicyclohexyl-1,7-dipiperidinylperylene-3,4:9,10- tetracarboxylic diimide (Ф = 0.2) as reference for compounds 4a and 4b. Methylene chloride containing 0.1 M tetra-n-butylammonium hexafluorophosphate (TBAPF6) was used as a solvent in electrochemical measurements. Ferrocene/ferrocenium redox couple (Fc/Fc+, V vs SCE in CH2Cl2) was used as an internal reference for all measurements. All electrochemical measurements were performed under dry nitrogen atmosphere using 0.1 V/s scan rate, the concentration of samples was 10-3 M. Melting points for all compounds exceeded 350 C, and could not be determined since above that temperature all the compounds started to decompose. S2
3 Figure S1. 1 H and 13 C { 1 H} spectra of Compound 1a. Note the presence of 2 carbonyl signals in 13 C NMR spectrum (around 165 ppm), and doubling of several aromatic signals. S3
4 Figure S2. 1 H and 13 C { 1 H} NMR spectra of compound 2a S4
5 Figure S3. 1 H NMR spectra: (a) regioisomeric mixture of 1,7-3a and 1,6-3a before recrystallization, (b) after three repetitive recrystallizations, (c) the mother liquor obtained in the first recrystallization (1,6-3a is a dominant species). Figure S4. 13 C { 1 H} NMR spectra, carbonyl peaks: (a) regioisomeric mixture of 1,7-3a and 1,6-3a before recrystallization, (b) after three repetitive recrystallizations (1,7-3a), (c) the mother liquor obtained in the first recrystallization (contains mostly 1,6-3a). Figure S5. 1 H NMR spectra: (a) regioisomeric mixture of 1,7-3b and 1,6-3b before recrystallization, (b) after three repetitive recrystallizations (pure 1,7-3b). S5
6 1 H and 13 C { 1 H} NMR spectra of compounds 2-5: S6
7 S7
8 S8
9 S9
10 S10
11 S11
12 S12
13 XYZ coordinates of the calculated compounds and transition states Geometry of complexes: PDI-Br2-Et-endo 70 C C C C C C C C N C C C C C C C C C C C C C C C N C O O C C C Br O C C H O C C H C H C C H H H H H Br H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-Br2-iPr-endo 82 S13
14 C C C C C C C C N C C C C C C C C C C C C C C C N C O O C C C Br O C C C O C C C C C C C C H H H H Br H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-Br2-iPr-exo S14
15 82 C C C C C N C C C C C C C C C C C C C C C C N C C C O C C C O Br O C C C O C C C C C C C C H H H H Br H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-Br-iPr-endo S15
16 82 C C C C C N C C C C C C C C C C C C C C C C N C C C O C C C O Br O C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S16
17 Geometry of complexes: PDI-Br-iPr-exo 82 C C C C C C C C N C C C C C C C C C C C C C C C N C O O C C C Br O C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S17
18 H Geometry of complexes: PDI-Cy-endo 72 C C C C C N C C C C C C C C C C C C C C C C N C C C O C C C O O C C C O C C H C C H H H H H H H H H H H H H H H H H H H C H H H H H C H H H H H Geometry of complexes: PDI-Cy-exo 72 S18
19 C C C C C C N C C C C C C C C C C C C C C C C C C N C C C C C C O O C C C C C C O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-Et-endo 70 C C C C C C C C S19
20 N C C C C C C C C C C C C C C C N C O O C C O C C O C C H H H C H C C C H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-Et-exo 70 C C C C C N C C C C C C C C C C C C S20
21 C C C C N C C C O C C C O O C C C O C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-iPr-endo 82 C C C C C C C C N C C C C C C C C C C C C C C C N C O O S21
22 C C C H O C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: PDI-iPr-exo 82 C C C C C N C C C C C C C C C C C C C C C C N C C C S22
23 O C C C O H O C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-CoreTwist-Br2-iPr-endo 82 C C C C C C C C N C C C C C C C C C C C C C C C S23
24 N C O O C C C O C C C O Br C C C C C C C C H H Br H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-CoreTwist-Br-iPr-endo 82 C C C C C N C C C C C C C C C C C C C C C C S24
25 N C C C O C C C O O C C C O C C C C C C C C H H H H H H H Br H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-ImideRotation-Br2-iPr 82 C C C C C C C C N C C C C C C C C C C C S25
26 C C C C N C O O C C C Br O C C C O C C C C C C C C H H H H Br H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-ImideRotation-Br-iPr 82 C C C C C N C C C C C C C C C C C C S26
27 C C C C N C C C O C C C O Br O C C C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-ImideRotation-Cy 72 C C C C C C N C C C C C C C C C S27
28 C C C C C C C C C C C C N C C C O C C C C C C O H O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H Geometry of complexes: TS-ImideRotation-Et 70 C C C C C C C C N C C C C C C C C C C C C C C C S28
29 N C O O C C O C C O C C C C H H H C H H H H H H H H H H H C H H H H H H H H H H H H H H H H Geometry of complexes: TS-ImideRotation-iPr 82 C C C C C C C C N C C C C C C C C C C C C C C C N C O O C C C O C C S29
30 C O C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S30
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