Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs
Tarek H. El-Assaad; Manuel Auer; Raul Castaneda; Kassem M. Hallal; Fadi M. Jradi; Lorenzo Mosca; Rony S. Khnayzer; Digambara Patra; Tatiana V. Timofeeva; Jean-Luc Bredas; Emil J. W. List-Kratochvil; Brigitte Wex; Bilal R. Kaafarani; Journal of Materials Chemistry C 4 (2016) 3041–3058; doi:10.1039/C5TC02849C

data_7234652
_publ_section_title
;
 Tetraaryl pyrenes: photophysical properties, computational studies,
 crystal structures, and application in OLEDs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3041
_journal_page_last               3058
_journal_paper_doi               10.1039/C5TC02849C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C40 H22 F4'
_chemical_formula_sum            'C40 H22 F4'
_chemical_formula_weight         578.61
_chemical_name_systematic        'Pyrene, 1,3,6,8-tetrakis(4-fluorophenyl)-'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.739(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.914(3)
_cell_length_b                   11.932(10)
_cell_length_c                   27.87(2)
_cell_measurement_temperature    100
_cell_volume                     1301.5(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9911
_diffrn_measured_fraction_theta_max 0.9911
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1239
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3961
_diffrn_reflns_theta_full        25.2493
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 
0.1441 before and 0.0753 after correction. The Ratio of minimum to maximum 
transmission is 0.6697. The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4763
_exptl_crystal_description       needle
_exptl_crystal_F_000             596.3492
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.5999
_refine_diff_density_min         -0.5095
_refine_diff_density_rms         0.1448
_refine_ls_d_res_high            0.8331
_refine_ls_d_res_low             4.6450
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0639
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0639
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.1071
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1628P)^2^+7.5855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2833
_refine_ls_wR_factor_ref         0.3119
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              -3
_reflns_number_gt                1807
_reflns_number_total             2336
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3041.cif
_cod_data_source_block           KNH-I-11C
_cod_original_cell_volume        1301.6(18)
_cod_database_code               7234652
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
;