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1 ELETRONI SUPPLEMENTARY INFORMATION Isomeric arbazolocarbazoles: Synthesis, haracterization and omparative Study in Organic Field Effect Transistors Miriam Más-Montoya, a Rocío Ponce Ortiz, bc David uriel,* a Arturo Espinosa, a Magali Allain, d Antonio Facchetti* b and Tobin J. Marks* b a Department of Organic hemistry, Faculty of hemistry, University of Murcia, ampus of Espinardo, Murcia, Spain. Fax: ; Tel: ; davidcc@um.es b Department of hemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States; a- facchetti@northwestern.edu, t-marks@northwestern.edu c Departamento de Química-Física, Facultad de iencias, ampus de Teatinos Málaga, Spain. d Laboratory of hemistry, Molecular Engineering of Angers (IMA), UMR NRS 6200 University of Angers, 2, Boulevard Lavoisier, Angers cedex, France. General. S1 1 and 13 NMR spectra..... S2 UV-visible spectra... S13 yclic Voltammetry... S13 Output characteristics S13 XRD. S14 AFM images. S15 omputational details.. S16 alculated structures.... S16 References S23 X-ray single-crystal diffraction data were collected at 293K on a diffractometer, equipped with a graphite monochromator utilizing MoKα radiation (λ = Å). The structure were solved by direct methods and refined on F2 by full-matrix least-squares method, using SELX97 (G.M. Sheldrick, 1998) package. All non-hydrogen atoms were refined anisotropically and absorption was corrected by SADABS program. The atoms were found by Fourier difference map for 14 and 16 and were treated as a riding model for 15. Thin films diffraction data were analyzed using wide-angle X-ray diffractometry (WAXRD) using standard /2 techniques, with monochromated ukα radiation. For further film characterization, tapping-mode AFM images were recorded. S1
2 Figure S1. 1 and 13 NMR spectra of compound 6. S2
3 Figure S2. 1 and 13 NMR spectra of compound 7. S3
4 Figure S3. 1 and 13 NMR spectra of compound 8. S4
5 Figure S4. 1 and 13 NMR spectra of compound 9. S5
6 Figure S5. 1 and 13 NMR spectra of compound 10. S6
7 Figure S6. 1 and 13 NMR spectra of compound 11. S7
8 Figure S7. 1 and 13 NMR spectra of compound 12. S8
9 Figure S8. 1 and 13 NMR spectra of compound 13. S9
10 Figure S9. 1 and 13 NMR spectra of compound 14. S10
11 Figure S10. 1 and 13 NMR spectra of compound 15. S11
12 Figure S11. 1 and 13 NMR spectra of compound 16. S12
13 Figure S12. UV-vis spectra recorded in 2 l M and thin film. Figure S13. yclic voltammetry recordedd at different scan rates of compound 10 (left) and 15 (right). Figure S14. Transfer characteristics for top-contact/bottom-gate OFETs O of compounds (a) 5 at 90º, (b) 14 at 90 º and (c) 16 at 25º, measured under vacuum. S13
14 Figure S15. Simulated (dotted line) and experimental (continuous line) XRD patterns of compounds (a) 5 at 90º, (b) 14 at 90 º and (c) 15 at 60º. Figure S16. XRD patterns. S14
15 Figure S17. Tapping mode AFM images of evaporated films on MDS-treated Si/SiO 2 substrates at the specified temperatures measured on a 5 mx5 m surface s area.. S15
16 omputational details Quantum chemical calculations were performed with the ORA electronic structure program package. 1 All geometry optimizations were run in redundant internal coordinates with tight convergence criteria, 2 using the B3LYP 3 functional together with the new efficient RIJOSX algorithm 4 and the def2-tzvp basis set. 5 Solvent effects ( 2 l 2 ) were taken into account via the OSMO solvation model. 6 From these geometries all reported data were obtained by means of single-point (SP) calculations using the same functional and the more polarized def2-tzvpp basis set. 7 Reported energies are uncorrected for the zero-point vibrational term. A semiempirical correction accounting for the major part of the contribution of dispersion forces to the energy was included. 8 alculated structures artesian coordinates (in Å) and energies for all computed species. 5 ( 2 ) E = au N N O O S16
17 5 + ( 2 ) E = au N N O O ( i ) E = au N S17
18 N O O ( i ) E = au S18
19 N N O O ( i ) E = au N N O O S19
20 14 ( 2h ) E = au N N ( 2h ) E = au N N S20
21 15 ( 2h ) E = au N N S21
22 16 ( 2h ) E = au N N S22
23 References 1 ORA an ab initio, density functional and semiempirical program package. Written by F. Neese. Version 2.8.0, Universität Bonn, Web page: 2 Tight convergence criteria for optimizations in ORA: energy change hartree; maximum gradient hartree/a 0 ; RMS gradient hartree/a 0 ; maximum displacement a 0 ; RMS displacement a 0. 3 A. D. Becke, J. hem. Phys., 1993, 98, 5648;. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, F. Neese, F. Wennmohs, A. ansen, U. Becker, hem. Phys., 2009, 356, F. Weigend, R. Ahlrichs, Phys. hem. hem. Phys., 2005, 7, A. Klamt, G. Schüürmann, J. hem. Soc. Perkin Trans. 2, 1993, 220, 799; A. Klamt, J. Phys. hem., 1995, 99, A. Schäfer,. uber, R. Ahlrichs, J. hem. Phys., 1994, 100, 5829; basis sets may be obtained from the Basis Set Exchange (BSE) software and the EMSL Basis Set Library: D. Feller, J. omp. hem., 1996, 17, S. Grimme, J. omput. hem., 2004, 25, 1463; S. Grimme, J. omput. hem., 2006, 27, S23
Spain c Departament de Química Orgànica, Universitat de Barcelona, c/ Martí I Franqués 1-11, 08080, Barcelona, Spain.
a Institute of Chemical Research of Catalonia, Av. Països Catalans, 16, 43007 Tarragona, Spain. b Departament de Química, Universitat Autònoma de Barcelona, Cerdanyola del Vallès, E-08193 Barcelona, Spain
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