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_7234655
_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         'C32 H18 S4'
_chemical_formula_sum            'C32 H18 S4'
_chemical_formula_weight         530.70
_chemical_name_systematic
'Thiophene, 2,2',2'',2'''-(1,3,6,8-pyrenetetrayl)tetrakis-'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 111.999(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.688(3)
_cell_length_b                   8.4634(16)
_cell_length_c                   10.987(2)
_cell_measurement_reflns_used    7652
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.89
_cell_volume                     1180.1(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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15254
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0508 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.9460.
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    1.493
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
;
Re-crystallisation from solvent: Vapor diffusion of chlorobenze
 in dichloromethane
;
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.3889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                3026
_reflns_number_total             3434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3041.cif
_cod_data_source_block           kmh-i-15b
_cod_original_cell_volume        1180.2(4)
_cod_database_code               7234655
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C5B-C1
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C5) = Uanis(C5B)
Uanis(C17) = Uanis(C1A)
4. Others
 Sof(C5)=Sof(C1A)=Sof(H1A)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(S2B)=1-
 FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(C5B)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C13(H13), C15(H15), C16(H16), C17(H17), C3(H3), C2(H2),
 C11(H11), C1A(H1A), C2B(H2B), C3B(H3B)
;