Synthesis of dual-state emissive twisted donor–acceptor fluorophores: tunable fluorescence and self-reversible mechanofluorochromism
Ravi, Sasikala; Priyadharsan, R. Rameshbabu; Karthikeyan, Subramanian; Pannipara, Mehboobali; Al-Sehemi, Abdullah G.; Moon, Dohyun; Anthony, Savarimuthu Philip; CrystEngComm 27 (2025) 2759–2766; doi:10.1039/D4CE01317D

data_7250177
_publ_section_title
;
 Synthesis of dual-state emissive twisted donor--acceptor fluorophores:
 tunable fluorescence and self-reversible mechanofluorochromism
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2759
_journal_page_last               2766
_journal_paper_doi               10.1039/D4CE01317D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C29 H20 N4 O2'
_chemical_formula_weight         456.49
_chemical_name_systematic
'(E)-2-cyano-3-(2-(2-cyanophenoxy)-4-(diphenylamino) phenyl)acrylamide'
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-12-19 deposited with the CCDC.	2025-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                76.39(3)
_cell_angle_beta                 74.05(3)
_cell_angle_gamma                83.35(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6580(17)
_cell_length_b                   10.746(2)
_cell_length_c                   13.271(3)
_cell_measurement_reflns_used    67815
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      0.361
_cell_volume                     1152.1(5)
_computing_cell_refinement       '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_data_collection
'<i>PAL BL2D-SMDC Program</i>(Shin et.al, 2016)'
_computing_data_reduction        '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    '<i>DIAMOND 4</i>(Putx&Brandenburg, 2014)'
_computing_publication_material  '<i>publCIF</i>(Westrip, 2010)'
_computing_structure_refinement  '<i>SHELXL-2018</i>(Sheldrick, 2018)'
_computing_structure_solution    '<i>SHELXT-2018</i>(Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.448
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'<i>HKL3000sm Scalepack</i>(Otwinowski et.al,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.059
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.275(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0602P)^2^+0.2099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5239
_reflns_number_total             6477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01317d2.cif
_cod_data_source_block           SPA945
_cod_depositor_comments
'Adding full bibliography for 7250174--7250178.cif.'
_cod_database_code               7250177
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.996
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              39982