High-Performance Solution-Processed Solar Cells and Ambipolar Behavior in Organic Field-Effect Transistors with Thienyl-BODIPY Scaffoldings
Thomas Bura; Nicolas Leclerc; Sadiara Fall; Patrick Lévêque; Thomas Heiser; Pascal Retailleau; Sandra Rihn; Antoine Mirloup; Raymond Ziessel; Journal of the American Chemical Society 134 (2012) 17404–17407; doi:10.1021/ja3072513

data_4118801
_publ_contact_author_address
;Laboratoire de Chimie Organique et Spectroscopies Avanc\'ees (LCOSA)
CNRS,  Ecole de Chimie, Polym\`eres, Mat\'eriaux de Strasbourg (ECPM)
25 rue Becquerel
67087 Strasbourg, Cedex 02
France
;
_publ_contact_author_email       ziessel@unistra.fr
_publ_contact_author_fax         +331
_publ_contact_author_name        'Ziessel, Raymond'
_publ_contact_author_phone       +331
_publ_section_title
;
 High-Performance Solution-Processed Solar Cells and Ambipolar Behavior in
 Organic Field-Effect Transistors with Thienyl-BODIPY Scaffoldings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17404
_journal_page_last               17407
_journal_paper_doi               10.1021/ja3072513
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C49 H50 B F2 I N2 S4'
_chemical_formula_sum            'C49 H50 B F2 I N2 S4'
_chemical_formula_weight         970.86
_chemical_name_systematic
; 
 5,5-difluoro-3-((E)-2-(4'-hexyl-[2,2'-bithiophen]-5-yl)vinyl)-7-
((E)-2-(5-hexyl-[2,3'-bithiophen]-5'-yl)
vinyl)-10-(4-iodophenyl)-1,9-dimethyl-5H-dipyrrolo[1,2-c:2',1'-f]
[1,3,2]diazaborinin-4-ium-5-uide 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             04-04-12
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.999(6)
_cell_angle_beta                 71.602(5)
_cell_angle_gamma                83.461(6)
_cell_formula_units_Z            2
_cell_length_a                   12.0762(8)
_cell_length_b                   13.2664(8)
_cell_length_c                   15.0653(11)
_cell_measurement_reflns_used    9315
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      69.0
_cell_measurement_theta_min      3.1
_cell_volume                     2256.6(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.1023
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19611
_diffrn_reflns_theta_full        53.99
_diffrn_reflns_theta_max         53.99
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    7.658
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       'squared plate'
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         5424
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                3376
_reflns_number_total             5424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3072513_si_002.cif
_cod_data_source_block           tb352_f1_in_solution
_cod_database_code               4118801