#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/4/4000471.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4000471 _journal_name_full 'Chemistry of Materials' _journal_year 2004 _publ_section_title ; Organic Micro-Electronics : Design, Synthesis, and Characterizaton of Ladder Oligo(para-aniline)s ; loop_ _publ_author_name 'Salem Wakim' 'Jimmy Bouchard' 'Michel Simard' 'Nicolas Drolet' 'Ye Tao' 'Mario Leclerc' _chemical_name_systematic ; 5,11-dioctyl-6,12-dimethylindolo[3,2-b]carbazole ; _chemical_melting_point 151 _chemical_formula_moiety 'C36 H48 N2' _chemical_formula_sum 'C36 H48 N2' _chemical_formula_weight 508.76 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3266(4) _cell_length_b 9.5576(6) _cell_length_c 15.3294(9) _cell_angle_alpha 96.841(4) _cell_angle_beta 92.152(4) _cell_angle_gamma 102.594(4) _cell_volume 754.59(9) _cell_formula_units_Z 1 _publ_section_abstract ; Ladder oligo(para-aniline) was prepared by Cadogan ring closure using N-alkyl-2-substituted carbazole precursor. This efficient synthetic methodology offers the opportunity to develop a new promoting class of materials for micro and nano-electronics. X-ray structure of this ladder demonstrates interesting \p-stacking arrangement of molecules along the a-axis of the single-crystal unit cell, with 3.45 \%A as intermolecular ring distance. Electrochemical studies which shows a good stability, as well as absorption and fluorescence studies of this oligomer are presented. The first OFET using ladder oligo(p-aniline) as an active layer has been successfully fabricated. It shows p-channel characteristics with a mobility of 10^-3^ cm^2^ V^-1^ s^-1^ and I~on~/I~off~ ratio of 105. ; _publ_section_exptl_prep ; 5-11-dioctyl-6,12-dimethylindolo[3,2-b]carbazole : A two-necked 250 mL flask fitted with condenser, magnetic stirring bar was charged with 146 mg (0.37 mmol) of 5-octyl-6,12-dimethylindolo[3,2-b]carbazole, 107 mg (0.56 mmol) of 1-bromooctane, 30 mg (0.74 mmol) of sodium hydroxide, 4 mg (11.10-3 mmol) of tetrabutylamonium hydrogensulfate (TBAH) and 6 mL of anhydrous acetone. The resulting mixture was refluxed overnight under argon and then poured into 5 mL of distillated water, and extracted three times with a mixture of THF and diethyl ether. The combined organic fractions were washed with water, dried over magnesium sulfate and the solvent was removed under reduced pressure. Recristallization from acetone afforded 167 mg of the title product as a yellow solid (Yield: 90%). M.P. 152^o^C. ; _publ_section_exptl_refinement ; All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H atoms were generated geometrically (C-H 0.94 to 0.98\%A) and were included in the refinement in the riding model approximation. Their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 2000). ; _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 4839 _cell_measurement_theta_min 5.8 _cell_measurement_theta_max 127.6 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method none _exptl_crystal_F_000 278 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7460 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART 2K/Platform' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 47 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 'see text' _diffrn_standards_decay_% 0.06 _diffrn_reflns_number 9563 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 63.96 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 63.96 _diffrn_measured_fraction_theta_full 0.965 _reflns_number_total 2412 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1616P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 'not refined' _refine_ls_number_reflns 2412 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2251 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.3099(4) 0.4078(3) 0.37463(13) 0.0768(7) Uani 1 1 d . . . C1 C 0.2972(6) 0.1567(4) 0.3064(2) 0.0933(10) Uani 1 1 d . . . H1 H 0.4401 0.1830 0.2729 0.112 Uiso 1 1 calc R . . C2 C 0.1682(7) 0.0146(4) 0.3023(2) 0.1047(10) Uani 1 1 d . . . H2 H 0.2235 -0.0575 0.2658 0.126 Uiso 1 1 calc R . . C3 C -0.0452(7) -0.0232(4) 0.3522(2) 0.1032(10) Uani 1 1 d . . . H3 H -0.1337 -0.1205 0.3481 0.124 Uiso 1 1 calc R . . C4 C -0.1265(6) 0.0796(4) 0.4066(2) 0.0905(9) Uani 1 1 d . . . H4 H -0.2715 0.0525 0.4391 0.109 Uiso 1 1 calc R . . C5 C 0.0036(5) 0.2242(3) 0.41447(17) 0.0759(8) Uani 1 1 d . . . C6 C 0.2116(5) 0.2601(4) 0.36108(17) 0.0779(8) Uani 1 1 d . . . C7 C 0.1693(4) 0.4710(3) 0.43747(15) 0.0704(8) Uani 1 1 d . . . C8 C -0.0217(5) 0.3567(3) 0.46486(16) 0.0713(8) Uani 1 1 d . . . C9 C -0.1918(4) 0.3846(3) 0.52971(16) 0.0716(8) Uani 1 1 d . . . C10 C -0.3740(5) 0.2580(3) 0.56051(18) 0.0878(9) Uani 1 1 d . . . H10A H -0.4215 0.2861 0.6194 0.132 Uiso 1 1 calc R . . H10B H -0.2898 0.1778 0.5610 0.132 Uiso 1 1 calc R . . H10C H -0.5277 0.2289 0.5208 0.132 Uiso 1 1 calc R . . C11 C 0.5496(5) 0.4727(3) 0.33651(16) 0.0794(8) Uani 1 1 d . . . H11A H 0.6612 0.4034 0.3326 0.095 Uiso 1 1 calc R . . H11B H 0.6392 0.5584 0.3763 0.095 Uiso 1 1 calc R . . C12 C 0.5106(5) 0.5163(3) 0.24578(16) 0.0793(8) Uani 1 1 d . . . H12A H 0.4107 0.5914 0.2499 0.095 Uiso 1 1 calc R . . H12B H 0.4116 0.4325 0.2064 0.095 Uiso 1 1 calc R . . C13 C 0.7657(5) 0.5730(3) 0.20705(16) 0.0764(8) Uani 1 1 d . . . H13A H 0.8697 0.6508 0.2494 0.092 Uiso 1 1 calc R . . H13B H 0.8586 0.4949 0.1993 0.092 Uiso 1 1 calc R . . C14 C 0.7427(5) 0.6298(3) 0.11965(16) 0.0815(8) Uani 1 1 d . . . H14A H 0.6406 0.5517 0.0770 0.098 Uiso 1 1 calc R . . H14B H 0.6481 0.7072 0.1272 0.098 Uiso 1 1 calc R . . C15 C 0.9955(5) 0.6872(3) 0.08221(16) 0.0789(8) Uani 1 1 d . . . H15A H 1.0894 0.6096 0.0746 0.095 Uiso 1 1 calc R . . H15B H 1.0978 0.7647 0.1252 0.095 Uiso 1 1 calc R . . C16 C 0.9761(5) 0.7452(3) -0.00494(18) 0.0807(8) Uani 1 1 d . . . H16A H 0.8853 0.6659 -0.0491 0.097 Uiso 1 1 calc R . . H16B H 0.8715 0.8180 0.0014 0.097 Uiso 1 1 calc R . . C17 C 1.2297(6) 0.8119(4) -0.0384(2) 0.0998(10) Uani 1 1 d . . . H17A H 1.3318 0.7381 -0.0468 0.120 Uiso 1 1 calc R . . H17B H 1.3234 0.8887 0.0068 0.120 Uiso 1 1 calc R . . C18 C 1.2101(7) 0.8743(4) -0.1231(2) 0.1175(12) Uani 1 1 d . . . H18A H 1.1314 0.7976 -0.1697 0.176 Uiso 1 1 calc R . . H18B H 1.3811 0.9201 -0.1382 0.176 Uiso 1 1 calc R . . H18C H 1.1051 0.9455 -0.1162 0.176 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0647(13) 0.0992(19) 0.0606(13) 0.0189(12) 0.0077(10) 0.0006(12) C1 0.087(2) 0.117(3) 0.0749(18) 0.0202(19) 0.0122(16) 0.0145(19) C2 0.117(3) 0.104(3) 0.089(2) 0.0055(19) 0.014(2) 0.018(2) C3 0.110(3) 0.096(2) 0.098(2) 0.015(2) 0.016(2) 0.006(2) C4 0.088(2) 0.098(2) 0.0805(19) 0.0185(18) 0.0090(16) 0.0051(18) C5 0.0670(16) 0.091(2) 0.0640(15) 0.0193(15) 0.0002(12) -0.0002(14) C6 0.0730(18) 0.094(2) 0.0628(15) 0.0156(15) 0.0047(13) 0.0071(16) C7 0.0603(16) 0.092(2) 0.0528(13) 0.0201(14) -0.0004(12) -0.0011(13) C8 0.0630(16) 0.085(2) 0.0588(14) 0.0195(14) -0.0050(12) -0.0028(13) C9 0.0592(15) 0.091(2) 0.0577(13) 0.0213(14) -0.0010(12) -0.0030(13) C10 0.0830(19) 0.097(2) 0.0728(16) 0.0203(15) 0.0121(14) -0.0092(16) C11 0.0597(16) 0.112(2) 0.0621(15) 0.0238(15) 0.0054(12) 0.0025(14) C12 0.0675(17) 0.106(2) 0.0596(14) 0.0211(14) 0.0020(12) 0.0043(14) C13 0.0656(16) 0.097(2) 0.0633(15) 0.0172(14) 0.0068(12) 0.0082(14) C14 0.0710(18) 0.105(2) 0.0666(16) 0.0218(15) 0.0081(13) 0.0099(15) C15 0.0743(18) 0.094(2) 0.0644(15) 0.0154(14) 0.0098(13) 0.0077(14) C16 0.0780(18) 0.095(2) 0.0686(16) 0.0161(14) 0.0142(13) 0.0142(15) C17 0.096(2) 0.120(3) 0.0771(18) 0.0251(18) 0.0184(16) 0.0025(18) C18 0.139(3) 0.134(3) 0.078(2) 0.031(2) 0.033(2) 0.014(2) _cod_database_code 4000471