Aroyl-S,N-ketene acetal-triarylamine bichromophores – intramolecular energy transfer and dual emission upon induced aggregation and encapsulation
El Abbassi, Abdelouahad; Krenzer, Julius; Petrov, Eugene P.; Biesen, Lukas; Vasylyeva, Vera; Merzenich, Sarah; Resch-Genger, Ute; Müller, Thomas J. J.; RSC Advances 16 (2026) 10255–10260; doi:10.1039/D5RA09361A

data_7251660
_publ_section_title
;
 Aroyl-S,N-ketene acetal-triarylamine bichromophores -- intramolecular
 energy transfer and dual emission upon induced aggregation and
 encapsulation
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              10255
_journal_page_last               10260
_journal_paper_doi               10.1039/D5RA09361A
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C34 H26 N2 O S'
_chemical_formula_sum            'C34 H26 N2 O S'
_chemical_formula_weight         510.63
_chemical_melting_point          375.15
_chemical_name_common            triphenylamine_aroyl-S,N-ketene_acetal
_chemical_name_systematic
(Z)-2-(3-(4-(diphenylamino)benzyl)benzo[d]thiazol-2(3H)-ylidene)-1-phenylethan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-09 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.25650(10)
_cell_length_b                   8.23820(10)
_cell_length_c                   19.28180(10)
_cell_measurement_reflns_used    26490
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.7970
_cell_measurement_theta_min      2.7120
_cell_volume                     2581.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -81.00  14.00   0.50    0.39    --  -46.76 102.00  90.00  190
  2  \w      8.00  81.00   0.50    0.39    --   46.76-102.00 -12.00  146
  3  \w    -81.00 -21.00   0.50    1.56    --  -91.75 102.00  90.00  120
  4  \w    106.00 178.00   0.50    1.56    --  113.25 102.00  90.00  144
  5  \w     43.00 106.00   0.50    1.56    --  113.25-102.00 -12.00  126
  6  \w    106.00 178.00   0.50    1.56    --  113.25 102.00  90.00  144
  7  \w   -118.00 -24.00   0.50    0.39    --  -46.76 -77.00 -30.00  188
  8  \w    -48.00  26.00   0.50    0.39    --  -46.76  38.00 -30.00  148
  9  \w    -28.00  21.00   0.50    0.39    --   46.76 -19.00  90.00   98
 10  \w    -28.00  21.00   0.50    0.39    --   46.76 -19.00-120.00   98
 11  \w     63.00 118.00   0.50    0.39    --   46.76 178.00-180.00  110
 12  \w    -28.00  21.00   0.50    0.39    --   46.76 -19.00 -30.00   98
 13  \w    -28.00  21.00   0.50    0.39    --   46.76 -19.00   0.00   98
 14  \w   -163.00 -77.00   0.50    1.56    --  -91.75 -57.00   0.00  172
 15  \w   -163.00 -78.00   0.50    1.56    --  -91.75 -53.00  16.97  170
 16  \w    -48.00 -19.00   0.50    1.56    --  -91.75  38.00-150.00   58
 17  \w    -48.00 -19.00   0.50    1.56    --  -91.75  38.00 -60.00   58
 18  \w    -48.00 -19.00   0.50    1.56    --  -91.75  38.00   0.00   58
 19  \w   -149.00 -78.00   0.50    1.56    --  -91.75 -52.00 103.94  142
 20  \w    -85.00 -23.00   0.50    1.56    --  -91.75 125.00-150.00  124
 21  \w   -115.00 -76.00   0.50    1.56    --  -91.75 -62.00  61.19   78
 22  \w    -64.00 -26.00   0.50    1.56    --  -91.75 125.00-180.00   76
 23  \w   -121.00 -75.00   0.50    1.56    --  -91.75 -62.00  90.91   92
 24  \w   -147.00-119.00   0.50    1.56    --  -91.75 -52.00 103.94   56
 25  \w    -62.00 -19.00   0.50    1.56    --  -91.75  57.00 -60.00   86
 26  \w    -65.00 -25.00   0.50    1.56    --  -91.75  57.00  30.00   80
 27  \w   -158.00 -83.00   0.50    1.56    --  -91.75 -52.00  34.80  150
 28  \w   -145.00-100.00   0.50    1.56    --  -91.75-102.00 -12.00   90
 29  \w   -153.00-127.00   0.50    1.56    --  -91.75 -62.00  90.91   52
 30  \w     53.00 106.00   0.50    1.56    --  113.25 -99.00 -60.00  106
 31  \w     46.00 105.00   0.50    1.56    --  113.25 -99.00  30.00  118
 32  \w     44.00 106.00   0.50    1.56    --  113.25-125.00 -90.00  124
 33  \w     43.00  99.00   0.50    1.56    --  113.25 -77.00 -90.00  112
 34  \w     43.00  80.00   0.50    1.56    --  113.25 -77.00 150.00   74
 35  \w     76.00 102.00   0.50    1.56    --  113.25 -99.00  90.00   52
 36  \w     79.00 105.00   0.50    1.56    --  113.25 -99.00 150.00   52
 37  \w     46.00 107.00   0.50    1.56    --  113.25-125.00-180.00  122
 38  \w     48.00  94.00   0.50    1.56    --  113.25-125.00-120.00   92
 39  \w     72.00 104.00   0.50    1.56    --  113.25 -99.00-120.00   64
 40  \w     47.00  99.00   0.50    1.56    --  113.25-125.00   0.00  104
 41  \w     66.00 100.00   0.50    1.56    --  113.25 -77.00  30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0000700000
_diffrn_orient_matrix_UB_12      -0.1250667000
_diffrn_orient_matrix_UB_13      -0.0593852000
_diffrn_orient_matrix_UB_21      0.0385048000
_diffrn_orient_matrix_UB_22      0.1270986000
_diffrn_orient_matrix_UB_23      -0.0482787000
_diffrn_orient_matrix_UB_31      0.0866061000
_diffrn_orient_matrix_UB_32      -0.0563928000
_diffrn_orient_matrix_UB_33      0.0229487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38605
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.272
_diffrn_reflns_theta_min         2.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.347
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.8214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4914
_reflns_number_total             5340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09361a2.cif
_cod_data_source_block           triphenylamine_aroyl-SN-ketene_acetal
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '102 \%C' was changed to
'375.15' -- it was converted from degrees Celsius (C) to kelvins (K).

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7251660
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H26 N2 O S '
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C21(H21), C22(H22), C18(H18), C8(H8), C24(H24), C28(H28), C30(H30),
 C25(H25), C31(H31), C33(H33), C11(H11), C32(H32), C5(H5), C26(H26), C4(H4),
 C12(H12), C3(H3)
;
_shelx_res_checksum              29333
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.844