Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties.
Islam, Khadimul; Narjinari, Himani; Bisarya, Akshara; Kumar, Akshai; Organic & biomolecular chemistry 19 (2021) 9692–9704; doi:10.1039/d1ob01861b

data_7158367
_publ_section_title
;
 Multi-fold Sonogashira coupling: a new and convenient approach to obtain
 tetraalkynyl anthracenes with tunable photophysical properties.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9692
_journal_page_last               9704
_journal_paper_doi               10.1039/d1ob01861b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C50 H34 O4'
_chemical_formula_sum            'C50 H34 O4'
_chemical_formula_weight         698.77
_chemical_name_common            TMPEA
_chemical_name_systematic
2,6,9,10-tetrakis((2-methoxyphenyl)ethynyl)anthracene
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                75.898(4)
_cell_angle_beta                 83.094(4)
_cell_angle_gamma                83.357(4)
_cell_formula_units_Z            1
_cell_length_a                   4.6663(5)
_cell_length_b                   14.0000(16)
_cell_length_c                   14.5094(17)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.32
_cell_volume                     908.96(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22015
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            maroon
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane and Methanol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0470
_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^)+(0.1000P)^2^+0.5373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                1913
_reflns_number_total             3217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01861b2.cif
_cod_data_source_block           adki245_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158365--7158370.cif.'
_cod_database_code               7158367