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_7234651
_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         'C44 H34 S4'
_chemical_formula_sum            'C44 H34 S4'
_chemical_formula_weight         690.95
_chemical_name_common            1,3,6,8-Tetramethylthiopyrene
_chemical_name_systematic        'Pyrene, 1,3,6,8-tetrakis(methylthio)-'
_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                 114.8800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.4099(17)
_cell_length_b                   6.9907(7)
_cell_length_c                   16.3466(17)
_cell_measurement_reflns_used    2791
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      4.15
_cell_volume                     1701.2(3)
_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      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0595
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19655
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0588 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.8855.
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    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             724
_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         0.416
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0683P)^2^+0.5663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                3095
_reflns_number_total             5209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3041.cif
_cod_data_source_block           2
_cod_database_code               7234651
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;