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_7234653
_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         'C48 H18 F24'
_chemical_formula_sum            'C48 H18 F24'
_chemical_formula_weight         1050.62
_chemical_name_systematic
'Pyrene, 1,3,6,8-tetrakis[3,5-bis(trifluoromethyl)phenyl]-'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 92.154(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.795(5)
_cell_length_b                   14.347(14)
_cell_length_c                   28.88(3)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    100
_cell_measurement_theta_max      19.14
_cell_measurement_theta_min      4.34
_cell_volume                     1985(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1524
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            16994
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.6
_diffrn_reflns_theta_min         4.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0666 after correction.
The Ratio of minimum to maximum transmission is 0.8119.
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    1.7576
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             1045.0820
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Thiphene'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0764
_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^)+(0.0964P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.2068
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              -4
_reflns_number_gt                1992
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3041.cif
_cod_data_source_block           kmh-i-20e
_cod_original_cell_volume        1985(3)
_cod_database_code               7234653
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F11-C24 = F11A-C24 = F12-C24 = F10-C24 = F10A-C24 = F12A-C24
 1.34 with sigma of 0.02
 F11A-F12A = F10A-F12 = F10-F11
 2.15 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F11A) = Uanis(F12A) = Uanis(F10A) = Uanis(F11) = Uanis(F12) = Uanis(F10)
4. Others
 Sof(F11A)=Sof(F12A)=Sof(F10A)=1-FVAR(1)
 Sof(F10)=Sof(F12)=Sof(F11)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C13(H13), C4(H4), C8(H8), C1(H1), C20(H20), C22(H22),
 C18(H18)
;