Chiral Thermally Activated Delayed Fluorescence Emitters-Based Efficient Circularly Polarized Organic Light-Emitting Diodes Featuring Low Efficiency Roll-Off.
Liu, Ting-Ting; Yan, Zhi-Ping; Hu, Jia-Jun; Yuan, Li; Luo, Xu-Feng; Tu, Zhen-Long; Zheng, You-Xuan; ACS applied materials & interfaces 13 (2021) 56413–56419; doi:10.1021/acsami.1c16223

data_4519136
_publ_section_title
;
 Chiral Thermally Activated Delayed Fluorescence Emitters-Based Efficient
 Circularly Polarized Organic Light-Emitting Diodes Featuring Low
 Efficiency Roll-Off.
;
_journal_issue                   47
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              56413
_journal_page_last               56419
_journal_paper_doi               10.1021/acsami.1c16223
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C72 H71.09 N2 O6 S2'
_chemical_formula_sum            'C21.5 H21.5 N21.5 O21.5 S21.5'
_chemical_formula_weight         1614.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-04-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.660(3)
_cell_length_b                   20.017(4)
_cell_length_c                   52.343(10)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      46.03
_cell_measurement_theta_min      3.59
_cell_volume                     13265(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      190.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            51641
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.172
_diffrn_reflns_theta_min         3.594
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.674
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0838 after correction.
The Ratio of minimum to maximum transmission is 0.8813.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       block
_exptl_crystal_F_000             6536
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     872
_refine_ls_number_reflns         12134
_refine_ls_number_restraints     3434
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0825P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                7830
_reflns_number_total             12134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am1c16223_si_003.cif
_cod_data_source_block           111_a
_cod_original_cell_volume        13264(5)
_cod_original_formula_sum        'C21.50 H21.50 N21.50 O21.50 S21.50'
_cod_database_code               4519136
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6A-C7A
 2.3 with sigma of 0.02
 C6A-C0
 2.3 with sigma of 0.02
 C7A-C0
 2.3 with sigma of 0.02
 C1AA-C3AA
 2.3 with sigma of 0.02
 C1AA-C2AA
 2.3 with sigma of 0.02
 C2AA-C3AA
 2.3 with sigma of 0.02
 C024-C025 \\sim C024-C0
 with sigma of 0.02
 C024-C6 \\sim C024-C6A
 with sigma of 0.02
 C024-C7 \\sim C024-C7A
 with sigma of 0.02
 C023-C4 \\sim C023-C4A
 with sigma of 0.02
 C023-C0AA \\sim C023-C0AB
 with sigma of 0.02
 C01F-C01Z \\sim C01F-C01{
 with sigma of 0.02
 C01F-C021 \\sim C01F-C2
 with sigma of 0.02
 C01F-C022 \\sim C01F-C1
 with sigma of 0.02
 C01K-C01O \\sim C01K-C2AA
 with sigma of 0.02
 C01K-C01W \\sim C01K-C1AA
 with sigma of 0.02
 C01K-C01X \\sim C01K-C3AA
 with sigma of 0.02
 C023-C5 \\sim C023-C5A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3A with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=
 Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(H0C)=1-FVAR(1)
 Sof(C025)=Sof(H02F)=Sof(H02G)=Sof(H02H)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(1)
 Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=
 Sof(C0AB)=Sof(H0AE)=Sof(H0AF)=Sof(H0AG)=1-FVAR(2)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C0AA)=Sof(H0AB)=Sof(H0AC)=Sof(H0AD)=
 Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C01{)=Sof(H1AA)=Sof(HD)=Sof(HE)=
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(3)
 Sof(C01Z)=Sof(C021)=Sof(C022)=Sof(H02C)=Sof(H02D)=Sof(H02E)=FVAR(3)
 Sof(C1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H1AD)=Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=Sof(C3AA)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(4)
 Sof(C01O)=Sof(H01L)=Sof(H01M)=Sof(H01O)=Sof(C01W)=Sof(H01Z)=Sof(H)=Sof(HA)=
 Sof(C01X)=Sof(H01)=Sof(HB)=Sof(HC)=FVAR(4)
7.a Riding coordinates:
 C5A(H5AA,H5AB,H5AC)
7.b Secondary CH2 refined with riding coordinates:
 C016(H01A,H01B), C01H(H01F,H01G), C01L(H01H,H01K), C01R(H01P,H01R), C01S(H01S,
 H01T), C01T(H01U,H01V), C01V(H01X,H01Y), C020(H02A,H02B)
7.c Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C00S(H00S), C00T(H00T), C00X(H00X), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C01B(H01C),
 C01C(H01D), C01D(H01E), C01I(H01I), C01J(H01J), C01N(H01N), C01Q(H01Q),
 C01U(H01W), C01Y(H0AA)
7.d Idealised Me refined as rotating group:
 C01O(H01L,H01M,H01O), C01W(H01Z,H,HA), C01X(H01,HB,HC), C022(H02C,H02D,H02E),
 C025(H02F,H02G,H02H), C6(H6A,H6B,H6C), C4(H4A,H4B,H4C), C0AA(H0AB,H0AC,H0AD),
 C7(H7A,H7B,H7C), C5(H5A,H5B,H5C), C7A(H7AA,H7AB,H7AC), C6A(H6AA,H6AB,H6AC),
 C0(H0A,H0B,H0C), C4A(H4AA,H4AB,H4AC), C0AB(H0AE,H0AF,H0AG), C1(H1A,H1B,H1C),
 C01{(H1AA,HD,HE), C2(H2A,H2B,H2C), C1AA(H1AB,H1AC,H1AD), C2AA(H2AA,H2AB,H2AC),
 C3AA(H3AA,H3AB,H3AC)
;
_olex2_submission_special_instructions 'No special instructions were received'