Synthesis and Characterization of New 2,3-Disubstituted Thieno[3,4-b]pyrazines: Tunable Building Blocks for Low Band Gap Conjugated Materials

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1 SUPPORTING INFORMATION Synthesis and Characterization of New 2,3-Disubstituted Thieno[3,4-b]pyrazines: Tunable Building Blocks for Low Band Gap Conjugated Materials Li Wen, Jon P. Nietfeld, Chad M. Amb, and Seth C. Rasmussen* Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, ND 58105, USA. Fax: ; Tel: ; Table of Contents: I. General experimental details... S2 II. Figure S1. 1 H NMR spectrum of 5... S2 III. Figure S2. 13 C NMR spectrum of 5... S3 IV. Figure S3. 1 H NMR spectrum of 2... S3 V. Figure S4. 13 C NMR spectrum of 2... S3 VI. Synthesis of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione... S4 VII. Figure S5. 1 H NMR spectrum of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione...S4 VIII. Figure S6. 13 C NMR spectrum of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione... S4 IX. Figure S7. 1 H NMR spectrum of 3... S5 X. Figure S8. 13 C NMR spectrum of 3... S5 XI. Figure S9. 1 H NMR spectrum of 6a... S5 XII. Figure S C NMR spectrum of 6a... S6 XIII. Figure S11. 1 H NMR spectrum of 6b... S6 XIV. Figure S C NMR spectrum of 6b... S6 XV. Figure S13. 1 H NMR spectrum of 6c... S7 XVI. Figure S C NMR spectrum of 6c... S7 XVII. Figure S15. 1 H NMR spectrum of 7... S7 XVIII. Figure S C NMR spectrum of 7... S8 XIX. Figure S17. 1 H NMR spectrum of 8... S8 XX. Figure S C NMR spectrum of 8... S8 XXI. Figure S19. 1 H NMR spectrum of 9... S9 XXII. Figure S C NMR spectrum of 9... S9 XXIII. Figure S21. 1 H NMR spectrum of 4... S9 XXIV. Figure S C NMR spectrum of 4... S10 XXV. Figure S23. 1 H NMR spectrum of S10 XXVI. Figure S C NMR spectrum of S10 S1

2 XXVII. Figure S25. 1 H NMR spectrum of 11a...S11 XXVIII. Figure S C NMR spectrum of 11a... S11 XXIX. Figure S27. 1 H NMR spectrum of 11b... S11 XXX. Figure S C NMR spectrum of 11b... S12 XXXI. Figure S29. 1 H NMR spectrum of 11c... S12 XXXII. Figure S C NMR spectrum of 11c... S12 XXXIII. Figure S31. 1 H NMR spectrum of 11d... S13 XXXIV. Figure S C NMR spectrum of 11d... S13 XXXV. X-ray Crystallography... S13 XXXVI. Table S1. Crystal data, collection parameters, and refinement statistics for 2,3-bis(bromomethyl)thieno[3,4-b]pyrazine (4)... S14 XXXVII. Figure S33. Ellipsoid Plot of 4 at the 50% probability level... S14 XXXVIII. UV-visible spectroscopy... S14 XXXIX. Table S2. Full UV-vis data of new thieno[3,4-b]pyrazines... S15 XL. Electrochemistry... S16 XLI. Calculations... S16 XLII. Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines... S16 XLIII. References... S21 General experimental details. Chromatographic separations were performed using standard column methods with silica gel ( mesh). All reactions were performed under nitrogen. NMR spectra were obtained in CDCl 3 on a 400 MHz spectrometer and referenced to the chloroform signal. Figure S1. 1 H NMR spectrum of 5 S2

3 Figure S2. 13 C NMR spectrum of 5 Figure S3. 1 H NMR spectrum of 2 Figure S4. 13 C NMR spectrum of 2 S3

4 Synthesis of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione. The following is a modification of previously reported methods. 1 Liquid Br 2 (0.54 ml, 10 mmol) and 1,4-dioxiane (0.85 ml, 10 mmol) were mixed together to form an adduct, which was then dissolved in 20 ml of THF. This solution was added dropwise to 5 (0.84 g, 5 mmol) in THF (30 ml) cooled in an ice/salt bath. The reaction mixture was stirred for 3 hr, during which the solution was allowed to warm to room temperature. The solid residue was recovered by vacuum filtration and washed by hexane to give a light grey solid (85-90% yield); mp 275 C (dec); 1 H NMR (d-dmso): δ (s, 2H); 13 C NMR (d- DMSO): δ 135.6, 127.4, Figure S5. 1 H NMR spectrum of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione Figure S6. 13 C NMR spectrum of 5,7-dibromothieno[3,4-b]pyrazine-2,3(1H,4H)-dione S4

5 Figure S7. 1 H NMR spectrum of 3 Figure S8. 13 C NMR spectrum of 3 Figure S9. 1 H NMR spectrum of 6a S5

6 Figure S C NMR spectrum of 6a Figure S11. 1 H NMR spectrum of 6b Figure S C NMR spectrum of 6b S6

7 Figure S13. 1 H NMR spectrum of 6c Figure S C NMR spectrum of 6c Figure S15. 1 H NMR spectrum of 7 S7

8 Figure S C NMR spectrum of 7 Figure S17. 1 H NMR spectrum of 8 Figure S C NMR spectrum of 8 S8

9 Figure S19. 1 H NMR spectrum of 9 Figure S C NMR spectrum of 9 Figure S21. 1 H NMR spectrum of 4 S9

10 Figure S C NMR spectrum of 4 Figure S23. 1 H NMR spectrum of 10 Figure S C NMR spectrum of 10 S10

11 Figure S25. 1 H NMR spectrum of 11a Figure S C NMR spectrum of 11a Figure S27. 1 H NMR spectrum of 11b S11

12 Figure S C NMR spectrum of 11b Figure S29. 1 H NMR spectrum of 11c Figure S C NMR spectrum of 11c S12

13 Figure S31. 1 H NMR spectrum of 11d Figure S C NMR spectrum of 11d X-ray Crystallography. X-ray quality crystals of 4 were grown by the slow evaporation of an acetonitrile solution. The X-ray intensity data of the crystals were measured at 273 K on a CCD-based X-ray diffractometer system equipped with a Mo-target X-ray tube (λ = Å) operated at 2000 W of power. The detector was placed at a distance of cm from the crystal. Frames were collected with a scan width of 0.3 in ω and exposure time of 10 s/frame and then integrated with the Bruker SAINT software package using an arrow-frame integration algorithm. The unit cell was determined and refined by least-squares upon the refinement of XYZ-centeroids of reflections above 20σ(I). The structure was refined using the Bruker SHELXTL (Version 5.1) Software Package. The crystal data, S13

14 data collection parameters, and refinement statistics are listed in Table S1. Full crystallographic data is included in the cif file. Table S1. Crystal data, collection parameters, and refinement statistics for 2,3-bis(bromomethyl)thieno[3,4-b]pyrazine (4). Formula C 8 H 6 Br 2 N 2 S Formula Weight Temperature (K) 273(2) Crystal System Space Group Orthorhombic Pca2(1) a (Å) (9) b (Å) (10) c (Å) 7.715(6) α (º) β (º) γ (º) V (Å 3 ) (14) Z 4 d calc (g cm -3 ) µ (mm -1 ) Reflections collected 8403 Unique reflections 2396 [R int = ] Final R indices [I>2σ(I)] R 1 = wr 2 = R indices (all data) a R 1 = wr 2 = Goodness-of-fit on F a R 1 = Σ( F o F c ) / Σ F o, wr 2 = [Σ(w(F o 2 F c 2 ) 2 ) / Σ(F o 2 ) 2 ] 1/2, Goodness-of-fit on F 2 = [Σ( w(f o 2 F c 2 ) 2 / (n-p)] 1/2, where n is the number of reflections and p is the number of parameters refined. 4 Figure S33. Ellipsoid Plot of 4 at the 50% probability level. S14

15 UV-visible spectroscopy. UV-visible spectra were measured on a dual beam scanning spectrophotometer using samples prepared as dilute CH 3 CN solutions in 1 cm quartz cuvettes. Oscillator strengths were determined from the visible spectra via spectral fitting to accurately quantify the area of each transition and then calculated using literature methods. 2 Table S2. Full UV-vis data of new thieno[3,4-b]pyrazines TP λ max (nm) ε (M -1 cm -1 ) f TP λ max (nm) ε (M -1 cm -1 ) f , c , , (sh) (sh) , (sh) , , , (sh) 13, (sh) , , (sh) , , , , (sh) (sh) 10, , (sh) 12, , a , , , , (sh) 9, , , (sh) , (sh) b , , , , (sh) 9, (sh) 6, , (sh) 11, , , S15

16 Table S2. Full UV-vis data of new thieno[3,4-b]pyrazines (continued) TP λ max (nm) ε (M -1 cm -1 ) f TP λ max (nm) ε (M -1 cm -1 ) f 11a , c , , , (sh) 6, (sh) , , b , d , , , (sh) (sh) Electrochemistry. Electrochemical measurements were performed on a BAS 100B/W using a Pt disc working electrode and a Pt wire counter electrode. Solutions consisted of 0.1 M TBAPF 6 in CH 2 Cl 2 or CH 3 CN and were sparged with argon for 20 min prior to data collection and blanketed with argon during the experiment. All potentials are referenced to either a Ag/Ag + reference, or a Ag wire quasi-reference electrode with an internal ferrocene reference. Calculations. All calculations were performed using Gaussian 03. Geometry optimization and frequency calculation of thieno[3,4-b]pyrazines were performed via Hartree-Fock calculations utilizing the 6-31G* basis set. The resulting calculated geometry agreed well with previously reported structural data. 7,14 Following optimization, HOMO/LUMO energies in relation to vacuum were calculated using DFT methods with 6-31G* basis set and a B3LYP correlation functional. Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines TP Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Energy (hartrees) 1a S16

17 Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines (continued) TP Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Energy (hartrees) 1d S17

18 Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines (continued) TP Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Energy (hartrees) S18

19 Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines (continued) TP Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Energy (hartrees) 6a S19

20 Table S3. Atom coordinates and absolute energies of calculated thieno[3,4-b]pyrazines (continued) TP Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Energy (hartrees) 11c S20

21 REFERENCES 1. Möhwald, H.; Belov, V.; Schrof, W. U.S. Patent 6,242,561 BI, June 5, N. J. Turro, Modern Molecular Photochemistry, University Science Books: Sausalito, CA, 1991, pp S21

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