Home Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
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Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO

  • Yunlu Li ORCID logo and Xinzhong Wang EMAIL logo
Published/Copyright: December 14, 2022

Abstract

C27H17NO, monoclinic, P21 (no. 4), a = 9.8945(6) Å, b = 8.1838(5) Å, c = 12.2042(7) Å, β = 107.539(6)°, V = 942.29(10) Å3, Z = 2, R gt (F) = 0.0306, wR ref (F 2) = 0.0698, T = 149.99(10)

CCDC no.: 2222147

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.14 × 0.13 × 0.11 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 5897, 2754, 0.025
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2617
N(param)refined: 263
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
O1 0.25718 (17) 0.5572 (3) −0.05836 (12) 0.0409 (5)
N1 0.32085 (18) 0.4016 (2) 0.38978 (14) 0.0227 (4)
C1 0.3992 (2) 0.4232 (3) 0.50568 (17) 0.0223 (5)
C2 0.5293 (2) 0.5002 (3) 0.55205 (19) 0.0269 (6)
H2 0.579660 0.546529 0.504510 0.032*
C3 0.5822 (3) 0.5062 (3) 0.6712 (2) 0.0314 (6)
H3 0.671470 0.556245 0.705892 0.038*
C4 0.5076 (3) 0.4408 (3) 0.74082 (19) 0.0306 (6)
H4 0.546670 0.447337 0.821972 0.037*
C5 0.3781 (3) 0.3666 (3) 0.69421 (18) 0.0275 (6)
H5 0.327043 0.324032 0.742450 0.033*
C6 0.3229 (2) 0.3548 (3) 0.57451 (17) 0.0214 (5)
C7 0.1938 (2) 0.2871 (3) 0.49799 (18) 0.0224 (5)
C8 0.1958 (2) 0.3200 (3) 0.38580 (18) 0.0222 (5)
C9 0.0866 (2) 0.2715 (3) 0.28978 (19) 0.0268 (6)
H9 0.089775 0.293785 0.214198 0.032*
C10 −0.0268 (2) 0.1897 (3) 0.3084 (2) 0.0294 (6)
H10 −0.103566 0.156296 0.244508 0.035*
C11 −0.0305 (3) 0.1554 (3) 0.4197 (2) 0.0311 (6)
H11 −0.109508 0.099096 0.430311 0.037*
C12 0.0795 (2) 0.2025 (3) 0.5144 (2) 0.0283 (6)
H12 0.077118 0.177279 0.589819 0.034*
C13 0.3532 (2) 0.4727 (3) 0.29414 (17) 0.0227 (5)
C14 0.4741 (2) 0.4232 (3) 0.27509 (17) 0.0237 (5)
H14 0.520974 0.334129 0.320910 0.028*
C15 0.5427 (2) 0.4871 (3) 0.19418 (18) 0.0235 (5)
C16 0.4724 (2) 0.5632 (3) 0.08974 (17) 0.0240 (5)
C17 0.3154 (2) 0.5792 (3) 0.04377 (17) 0.0267 (5)
C18 0.2339 (2) 0.6447 (3) 0.11848 (19) 0.0261 (6)
C19 0.2548 (2) 0.6010 (3) 0.23361 (18) 0.0236 (5)
C20 0.1727 (3) 0.6814 (3) 0.2929 (2) 0.0309 (6)
H20 0.183907 0.652569 0.370579 0.037*
C21 0.0766 (3) 0.8007 (3) 0.2418 (2) 0.0389 (7)
H21 0.024869 0.855434 0.284998 0.047*
C22 0.0548 (3) 0.8414 (4) 0.1276 (2) 0.0410 (7)
H22 −0.012834 0.922369 0.091547 0.049*
C23 0.1328 (2) 0.7627 (3) 0.0671 (2) 0.0344 (6)
H23 0.117392 0.789438 −0.011519 0.041*
C24 0.5501 (2) 0.6240 (3) 0.02033 (19) 0.0301 (6)
H24 0.501840 0.675938 −0.050221 0.036*
C25 0.6953 (3) 0.6099 (4) 0.0522 (2) 0.0349 (6)
H25 0.747317 0.655589 0.005730 0.042*
C26 0.7649 (3) 0.5284 (3) 0.1528 (2) 0.0324 (6)
H26 0.864880 0.515780 0.174350 0.039*
C27 0.6899 (2) 0.4655 (3) 0.22180 (19) 0.0285 (6)
H27 0.738757 0.406632 0.289188 0.034*

Source of materials

To a solution of 5-dibenzosuberenone (0.206 g, 1 mmol) in THF (15 mL), liquid Br2 (0.16 g) was added dropwise at 280 K for 30 min. Then the mixture was stirred at room temperature for 2 h. After the reaction was completed, the solvent was evaporated to give a crude intermediate product. A mixture of intermediate product (0.366 g, 1 mmol), carbazole (0.20 g, 1.2 mmol), potassium carbonate (0.277 g, 2.0 mmol), potassium iodide (0.033 g, 0.2 mmol) and THF (15 mL) was placed in a 50 mL sealed tube under nitrogen. The reaction mixture was stirred at 350 K for 36 h. After completion of the reaction, the mixture was passed through celite filtration, the extract was dried using magnesium sulphate, and then the solvent was removed under reduced pressure. The dried residue was then purified by silica gel column chromatography using an ethyl acetate/n-hexane mixture as eluent to give the desired sky blue colour compound, and recrystallized from methanol to obtain the title compound as colourless block crystals.

Experimental details

Hydrogen atoms were included using riding models implemented in the SHELXL software [3, 4]. Their U iso values were set to 1.2 U eq of the parent atoms. Using Olex2 [2], the structure was solved with the ShelXS [3] structure solution program using Direct Methods and refined with the ShelXL [4] refinement package.

Comment

Over the past three decades, organic light-emitting diodes (OLEDs) have experienced a rapid development [5]. But the development of blue OLEDs materials has been lagging behind due to the high excitation energy and aggregation caused-quenching (ACQ), triplet-triplet annihilation (TTA) and triplet-polar annihilation (TPA) [6]. Here, we designed a heptagonal core skeleton combining the weak electron-withdrawing group of benzophenone and electron-donating group of carbazole (Cz). The title compound has a good balance between rigidity and flexibility and effectively inhibits ACQ and TTA, which makes it a potential blue OLED.

The crystal struture of the title compound is similar with the reported structure [7] of 2-(9,9-dimethylacridin-10(9H-yl)-4-methyl-5H-dibenzo[a,d] [7] annelen-5-one. The three rings in dibenzosuberenone are not in the one plane, and the Cz group is almost perpendicular to the heptagonal skeleton. All the bond lengths and angles of this molecule are in the expected ranges.


Corresponding author: Xinzhong Wang, Department of Electronic Communication and Technology, Shenzhen Institute of Information Technology, 518172 Longxiang Avenue No. 2188, Longgang District, Shenzhen, P. R. China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Natural Science Foundation of China (No. 22105023), Science and Technology Project of Shenzhen City (JSGG20210802154213040).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Bruker. SAINT, APEX2 and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

4. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

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7. Ma, W., Bin, Z. Y., Yang, G., Liu, J. J., You, J. S. Structurally nontraditional bipolar hosts for RGB phosphorescent OLEDs: boosted by a butterfly-shaped medium ring acceptor. Angew. Chem. Int. Ed. 2022, 61, e202116681; https://doi.org/10.1002/anie.202116681.Search in Google Scholar PubMed

Received: 2022-10-09
Accepted: 2022-11-25
Published Online: 2022-12-14
Published in Print: 2023-01-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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