Energy level tuning of blue emitting and electron transporting vinylene bis(vinyl quinolinyl)benzene derivatives: synthesis, characterisation, thin film characterisation and performance in OLEDs
Poopathy Kathirgamanathan; Sivagnanasundram Surendrakumar; Seenivasagam Ravichandran; Muttulingam Kumaraverl; Juan Antipan Lara; Subramaniam Ganeshamurugan; Lisa M. Bushby; Jeremiah P. Tidey; Alexander J. Blake; Journal of Materials Chemistry C 3 (2015) 6652–6667; doi:10.1039/C5TC00932D

data_7234288
_publ_section_title
;
 Energy level tuning of blue emitting and electron transporting vinylene
 bis(vinyl quinolinyl)benzene derivatives: synthesis, characterisation,
 thin film characterisation and performance in OLEDs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              6652
_journal_page_last               6667
_journal_paper_doi               10.1039/C5TC00932D
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C28 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46
_chemical_name_systematic        'bis (vinyl quinolinyl)bBenzene'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                102.184(6)
_cell_angle_beta                 90.398(7)
_cell_angle_gamma                91.768(7)
_cell_formula_units_Z            2
_cell_length_a                   3.9847(4)
_cell_length_b                   11.5962(8)
_cell_length_c                   21.0935(13)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      70.0090
_cell_measurement_theta_min      4.2870
_cell_volume                     952.18(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
MERCURY, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, 
G. P. Shields, R. Taylor, M. Towler and J. van de Streek, 
J. Appl. Crystallogr. 2006, 39, 453
;
_computing_publication_material
;
OLEX2, L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, J. A. K. Howard
and H. Puschmann, Acta Crystallogr., Sect. A 2015, 71, 59. 
;
_computing_structure_refinement
;
SHELXL, G. M. Sheldrick, Acta Crystallogr., Sect. A 2015, 71, 3.
;
_computing_structure_solution
;
SHELXS, G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112.
;
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 8.0750
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9870
_diffrn_measurement_details
;
  1 omega   17.00   49.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 32

  2 omega  -32.00    1.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 33

  3 omega   22.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 47

  4 omega -135.00    8.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000  -12.0000  -30.0000 143

  5 omega -132.00 -107.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000 -104.0000 -180.0000 25

  6 omega -130.00 -105.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000 -123.0000 -131.0000 25

  7 omega  -81.00   16.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000   61.0000  -60.0000 97

  8 omega -133.00 -108.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000  -95.0000   60.0000 25

  9 omega  -42.00    6.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000   30.0000 -180.0000 48

 10 omega  -89.00  -18.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000   77.0000  120.0000 71

 11 omega  -20.00   25.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000   30.0000  -60.0000 45

 12 omega   23.00   50.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -150.0000 27

 13 omega   61.00  120.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -150.0000 59

 14 omega   38.00   96.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000    0.0000 58

 15 omega   42.00   70.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -150.0000 28

 16 omega   76.00  103.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -123.0000 -131.0000 27

 17 omega   50.00  104.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 54

 18 omega   50.00   84.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 34

 19 omega   61.00   88.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -120.0000 27

 20 omega   54.00   81.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   90.0000 27

 21 omega  134.00  177.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  138.0000  150.0000 43

 22 omega   88.00  175.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000    0.0000 87

 23 omega   93.00  122.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  138.0000  150.0000 29

 24 omega   39.00   72.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 33

 25 omega   43.00  104.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   60.0000 61

 26 omega   35.00  157.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000 -120.0000 122

 27 omega   82.00  126.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 44

 28 omega  143.00  176.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   60.0000 33

 29 omega   78.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  -30.0000 100

 30 omega   54.00  124.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000   60.0000 70

 31 omega  -37.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   90.0000 112

 32 omega  -37.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 112

 33 omega -130.00  -73.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000 -125.0000  -30.0000 57

 34 omega -132.00  -79.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -53.5000  -92.0000 -120.0000 53

 35 omega    5.00  135.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   30.0000 -120.0000 130

 36 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000    0.0000 112

 37 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   60.0000 112

 38 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -60.0000 112

 39 omega   23.00  120.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -90.0000 97

 40 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -150.0000 112

 41 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -90.0000 112

 42 omega   19.00  131.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 112

 43 omega   81.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   90.0000 97

 44 omega   72.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -120.0000 106

 45 omega   50.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -180.0000 128

 46 omega   72.00  162.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -90.0000 90

 47 omega   32.00  113.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -104.0000  -90.0000 81

 48 omega   75.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 103

 49 omega   72.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -150.0000 106

 50 omega   72.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -60.0000 106

 51 omega   75.00  178.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 103

 52 omega   32.00   94.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -90.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0186274000
_diffrn_orient_matrix_UB_12      0.1332113000
_diffrn_orient_matrix_UB_13      0.0019853000
_diffrn_orient_matrix_UB_21      -0.0314013000
_diffrn_orient_matrix_UB_22      0.0240816000
_diffrn_orient_matrix_UB_23      0.0743517000
_diffrn_orient_matrix_UB_31      0.3851151000
_diffrn_orient_matrix_UB_32      0.0129230000
_diffrn_orient_matrix_UB_33      0.0071918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.046
_diffrn_reflns_theta_min         3.902
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.035
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.1188
_exptl_crystal_size_mid          0.0667
_exptl_crystal_size_min          0.0245
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.7801P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2512
_reflns_number_total             3557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-6652.cif
_cod_data_source_block           E278-ST
_cod_database_code               7234288
_chemical_oxdiff_formula         'C28 H20 N2'
_chemical_oxdiff_usercomment
;
PKAJBB, 12752, for PK / AJB, yellow trapezoidal plate mounted in 
light fomblin on micromount
;
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C24(H24), C12(H12), C4(H4), C18(H18), C29(H29), C26(H26),
 C19(H19), C21(H21), C3(H3), C9(H9), C7(H7), C23(H23), C6(H6), C22(H22), C8(H8),
  C27(H27), C30(H30), C11(H11)
;
_shelx_res_checksum              44397