Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes Based on Boron-Substituted Diisoindolomethene Frameworks
Gilles Ulrich; Sébastien Goeb; Antoinette De Nicola; Pascal Retailleau; Raymond Ziessel; Journal of Organic Chemistry 76 (2011) 4489–4505; doi:10.1021/jo200246q

data_4026357
_publ_contact_author_address
;Laboratoire de Chimie
Universit\'e Louis Pasteur, d'Electronique et de Photonique Moleculaires
ECPM, 1 rue Blaise Pascal
Strasbourg
F-67008
FRANCE

;
_publ_contact_author_email
gulrich@chimie.u-strasbg.fr;ziessel@chimie.u-strasbg.fr
_publ_contact_author_fax         0390242635
_publ_contact_author_name
;
Ulrich Gilles;Ziessel Raymond
;
_publ_contact_author_phone       0390242696
_publ_section_title
;
 Chemistry at Boron: Synthesis and Properties of Red to Near-IR
 Fluorescent Dyes Based on Boron-Substituted Diisoindolomethene Frameworks
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4489
_journal_page_last               4505
_journal_paper_doi               10.1021/jo200246q
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C49 H33 B N2, 0.5(C6 H12), 0.5(C2 H3 N)'
_chemical_formula_sum            'C53 H40.5 B N2.5'
_chemical_formula_weight         723.19
_chemical_name_systematic
; 
 ? 
;
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             31-08-06
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.78(2)
_cell_angle_beta                 110.03(2)
_cell_angle_gamma                102.17(2)
_cell_formula_units_Z            2
_cell_length_a                   11.294(4)
_cell_length_b                   13.299(3)
_cell_length_c                   14.735(4)
_cell_measurement_reflns_used    3263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.967
_cell_measurement_theta_min      0.998
_cell_volume                     1938.4(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997)  COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full .915
_diffrn_measured_fraction_theta_max .915
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans with kappa offsets'
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10488
_diffrn_reflns_theta_full        22.39
_diffrn_reflns_theta_max         22.39
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       'very thin plate'
_exptl_crystal_F_000             762
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_refine_diff_density_max         .223
_refine_diff_density_min         -.175
_refine_diff_density_rms         .039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         4574
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0649
_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^)+(0.1213P)^2^+0.1065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2000
_reflns_number_gt                3135
_reflns_number_total             4585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200246q_si_007.cif
_cod_data_source_block           compound_16_WIGQEJ
_cod_original_cell_volume        1938.4(10)
_cod_original_formula_sum        'C53 H40.50 B N2.50'
_cod_database_code               4026357