Home Physical Sciences The crystal structure of 6,6′-difluoro-3,3′-dimethyl-5,5′-di(10H-phenoxazin-10-yl)- [1,1′-biphenyl]-2,2′-dicarbonitrile, C40H24F2N4O2
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The crystal structure of 6,6′-difluoro-3,3′-dimethyl-5,5′-di(10H-phenoxazin-10-yl)- [1,1′-biphenyl]-2,2′-dicarbonitrile, C40H24F2N4O2

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Published/Copyright: July 8, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 5

Abstract

C40H24F2N4O2, monoclinic, P21/c (no. 14), a = 11.6521(4) Å, b = 11.6491(4) Å, c = 23.0401(7) Å, β = 102.824(1)°, V = 3,049.37 (18) Å3, Z = 4, Rgt(F) = 0.0431, wR ref (F2) = 0.1122, T = 190 K.

CCDC no.: 2429521

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

Table 1:

Data collection and handling.

Crystal: Block
Size: 0.16 × 0.07 × 0.06 mm
Wavelength: Ga Kα radiation (1.34139 Å)
μ: 0.50 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω scans
θmax, completeness: 53.9°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 21,409, 5,533, 0.046
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3,827
N(param)refined: 529
Programs: Bruker 1 Olex2 2 SHELX 3 , 4

1 Source of materials

According to previous literature reports, 5 the title compond can be synthesized from 5,5′,6,6′-tetrafluoro-3,3′-dimethyl-[1,1′-biphenyl]-2, 2′-dicarbonitrile (3.04 g, 10.0 mmol) and caesium carbonate (3.26 g, 10.0 mmol) and 10H-phenoxazine (3.66 g, 20.0 mmol) in N,N- dimethylformamide (DMF, 50 mL). The mixture was stirred and refluxed for 24 h. Cooling to room temperature, the mixture was extracted with water and ethyl acetate three times. The combined organic layer was concentrated and further purified by silica gel column chromatography to a red solid (4.48 g, 7.10 mmol, 71.0 % yield) and recrystallized from dichloromethane and methanol diffusion to obtain the title compound as red block crystals.

2 Experimental details

The structure was solved with the SHELXS 3 in OLEX2, 2 structure solution program using Direct Methods and refined with the SHELXL 4 refinement package. The Uiso values of hydrogen atoms (C–H) were set to 1.2 Ueq of the parent atoms. Their Uiso values of hydrogen atoms (C–H,H,H) were set to 2.5 Ueq. All hydrogen atoms were included via riding models implemented in the SHELXL software. 3 , 4

3 Comment

Thermally activated delayed fluorescence (TADF) materials have emerged as the third generation of organic light-emitting diodes emitters, garnering significant attention due to their theoretical achievement of 100 % internal quantum efficiency and cost-effectiveness without the reliance on precious metal elements. 6

The efficacy of TADF materials in harnessing triplet exciton emission stems from a substantial twist angle between their electron donor and acceptor moieties, thereby reducing the overlap integral of highest occupied molecular orbital and lowest unoccupied molecular orbital. This reduction facilitates a decrease in energy difference between singlet and triplet excited states. Through thermal activation, reverse intersystem crossing enables the transformation of triplet into singlet excitons, ultimately leading to delayed fluorescence emission. The title compound exhibits phenoxazines as electron donors and a benzonitrile derivative as an acceptor. The dihedral angles between them approach 90° (see the figure), indicating the potential for achieving TADF properties. Bond lengths and angles are all in the expected ranges. 7

Corresponding author: Bangjin Sun, Shenzhen Institute of Information Technology, 518172 Longxiang Avenue No.2188, Longgang District, Shenzhen, P.R. China, E-mail:

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

  2. Research funding: This work is supported by the China Postdoctoral Science Foundation (2022M710020).

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

References

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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. Cryst. 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 Cryst. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

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

5. Tu, Z.-L.; Lu, J.-J.; Luo, X.-F.; Hu, J.-J.; Li, S.; Wang, Y.; Zheng, Y.-X.; Zuo, J.-L.; Pan, Y. Blue Axially Chiral Biphenyl Based Thermally Activated Delayed Fluorescence Materials for Efficient Circularly Polarized Oleds. Adv. Opt. Mater. 2021, 9, 2100596; https://doi.org/10.1002/adom.202100596.Search in Google Scholar

6. Sun, B.; Ding, L.; Wang, X.; Tu, Z.-L.; Fan, J. Circularly Polarized Thermally Activated Delayed Fluorescence Oleds with Nearly BT.2020 Red Emission. Chem. Eng. J. 2023, 476, 146511; https://doi.org/10.1016/j.cej.2023.146511.Search in Google Scholar

7. Shin, S. Y.; Lee, H. J.; Koh, D. The Crystal Structure of Ethyl 2′-Hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7. Z. Kristallogr. - N. Cryst. Struct. 2023, 238, 149–151. https://doi.org/10.1515/ncrs-2022-0517.Search in Google Scholar
Received: 2025-03-14
Accepted: 2025-04-29
Published Online: 2025-07-08
Published in Print: 2025-10-27

© 2025 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (S)-N-(10-((2,2-dimethoxyethyl)amino)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide, C25H32N2O7
  4. The crystal structure of 6,6′-difluoro-3,3′-dimethyl-5,5′-di(10H-phenoxazin-10-yl)- [1,1′-biphenyl]-2,2′-dicarbonitrile, C40H24F2N4O2
  5. Crystal structure of poly[(di-ethylenediamine-κ2N,N′)cadmium(II) tetradedocyloxidohexavanadate] (V4+/V5+ = 2/1), C4H16CdN4O14V6
  6. The crystal structure of poly[bis(dimethylformamide-κ1N)-(μ4-2′,3,3″,5′-tetrakis(trifluoromethyl)-[1,1′:4′,1″-terphenyl]-4,4″-dicarboxylato-κ4 O,O′: O″,O‴)dicadmium(II)], C27H15CdF12NO5
  7. Crystal structure of bis(μ2-ferrocenylcarboxylato-O,O′)-(μ3-oxido-κ3O:O:O)-bis(μ2-salicyladoximato-κ2N,O,O′)-(μ2-isopropoxo)-tris(isopropoxy-κ1O trititanium(IV)), C48H55N2O13Fe2Ti3
  8. Crystal structure of 3-(diethylamino)-7,9,11-trimethyl-8-phenyl-6H,13H-12λ4,13λ4-chromeno[3′,4′:4,5]pyrrolo[1,2-c]pyrrolo[2,1-f][1,3,2]diazaborinin-6-one, C28H26BF2N3O2
  9. The crystal structure of catena-poly[aqua-μ2-2-nitro-benzene-1,3-dicarboxylato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)-zinc(II)], C20H13N3O7Zn
  10. Crystal structure of poly[diaqua-{μ3-1-(3-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ4O,O′:O′′:O′′′′}manganese(II)] hydrate
  11. Crystal structure of N′-((1-hydroxycyclohexyl)(phenyl)methyl)-2-methoxybenzohydrazide methanol solvate, C22H28N2O4
  12. The cocrystal of caffeic acid — progesterone — water (1/2/1), C51H70O9
  13. Crystal structure of (((oxido(quinolin-6-yl)methoxy)triphenyl-λ5-stibanyl)oxy)(quinolin-7-yl)methanolate
  14. Crystal structure of [(E)-6′-(diethylamino)-2-(2-(((E)-pyren-1-ylmethylene)amino)ethyl)-4′-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)-1′,2′,3′,4′-tetrahydrospiro[isoindoline-1,9′-xanthen]-3-one]-methanol, solvate C57H56N4O3
  15. The crystal structure of 1-(acridin-9-yl)pyrrolidine-2,5-dione, C17H22N2O2
  16. Crystal structure of N-(4-acetylphenyl)-2-(6-methoxynaphthalen-2-yl)propanamide, C22H21NO3
  17. The crystal structure of 5,10,15,20-tetrakis(4-(1H-1,2,4-triazol-1-yl)phenyl)porphyrin, C52H34N16
  18. Crystal structure of hexacarbonyl-μ2-[phenylmethanedithiolato-κ4S:S,S′:S′]diiron (Fe–Fe) C13H6Fe2O6S2
  19. Crystal structure of diiodo-bis(1-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ1N)cadmium(II), C34H34CdI2N10
  20. Crystal structure of (E)-(3-(3-bromophenyl)acryloyl)ferrocene, C19H15BrFeO
  21. Crystal structure of catena-poly(μ2-6-chloropyridine-2-carboxylato-κ3N,O:O′)(6-chloropyridine-2-carboxylato-κ2O,N)copper(II), C12H6Cl2N2O4Cu
  22. Crystal structure of poly[diaqua-μ 3-(5-(3,5-dicarboxy-2,4,6-trimethylbenzyl)-2,4,6-trimethylisophthalato)-κ 6O,O′:O″,O‴:O‴′,O‴″) terbium(III)-monohydrate], C23H28TbO12
  23. Crystal structure of (E)-2-(((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one – ethanol (1/2), C35H33ClN4O6
  24. The crystal structure of 3-(5-amino-3-phenylisoxazol-4-yl)-4-chloro-3-hydroxyindolin-2-one, C17H12ClN3O3
  25. The crystal structure of dimethylammonium 4-[2-(4-fluorophenyl)-4, 5-diphenyl-1H-imidazol-1-yl]benzenesulfonate, C29H26FN3O3S
  26. Crystal structure of (R)-2-ammonio-3-((5-carboxypentyl)thio)propanoate
  27. Crystal structure of 4-cyclohexyl-5-(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C12H15N3S2
  28. The crystal structure of 4,6-bis(dimethylamino)-2-fluoroisophthalonitrile, C12H13FN4
  29. Hydrogen bonding in the crystal structure of nicotin-1,1′-dium tetrabromidomanganate(II)
  30. The crystal structure of bis(2-bromobenzyl)(2-((2-oxybenzylidene)amino)-4-methylpentanoato-κ3N, O,O′)tin(IV), C27H27Br2NO3Sn
  31. Crystal structure of (E)-(3-(p-tolyl)acryloyl)ferrocene, C20H18FeO
  32. Crystal structure of (E)-7-fluoro-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C21H22FN3O
  33. Crystal structure of (E)-7-methoxy-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C22H25N3O2
  34. The crystal structure of poly(bis(μ2-1,3,5-tri(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-2,3,5,6-tetrafluoroterephthalato-κ2O:O′)-manganese(II), C38H24F4N12O4Mn
  35. Crystal structure of (3,4-dimethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO3P
  36. Crystal structure of tetraethylammonium hydrogencarbonate – (diaminomethylene)thiourea – water (2/1/3)
  37. Crystal structure of N, N-Dimethyl-N′-tosylformimidamide, C10H14N2O2S
  38. The crystal structure of ethyl 2-methyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H23N2O4
  39. Crystal structure of bis(μ2-1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene] thiocarbonohydrazide)-bis(dimethylformamide)-dizinc(II) dimethylformamide solvate, C40H46N10O6S2Zn2⋅C3H7NO
  40. Crystal structure of azido-κ1N{hydridotris(3-tert-butyl-5-methylpyrazol-1-yl)borato-κ3N,N′,N″}copper(II), C24H40BCuN9
  41. The crystal structure of fac-tricarbonyl(1,10-phenanthroline-κ2N,N′)-(azido-κ1N)rhenium(I), C15H8N5O3Re
  42. Crystal structure of 4-((triphenylphosphonio)methyl)pyridin-1-ium tetrachloridozincate(II), C24H22Cl4NPZn
https://doi.org/10.1515/ncrs-2025-0134
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (S)-N-(10-((2,2-dimethoxyethyl)amino)-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide, C25H32N2O7
  4. The crystal structure of 6,6′-difluoro-3,3′-dimethyl-5,5′-di(10H-phenoxazin-10-yl)- [1,1′-biphenyl]-2,2′-dicarbonitrile, C40H24F2N4O2
  5. Crystal structure of poly[(di-ethylenediamine-κ2N,N′)cadmium(II) tetradedocyloxidohexavanadate] (V4+/V5+ = 2/1), C4H16CdN4O14V6
  6. The crystal structure of poly[bis(dimethylformamide-κ1N)-(μ4-2′,3,3″,5′-tetrakis(trifluoromethyl)-[1,1′:4′,1″-terphenyl]-4,4″-dicarboxylato-κ4 O,O′: O″,O‴)dicadmium(II)], C27H15CdF12NO5
  7. Crystal structure of bis(μ2-ferrocenylcarboxylato-O,O′)-(μ3-oxido-κ3O:O:O)-bis(μ2-salicyladoximato-κ2N,O,O′)-(μ2-isopropoxo)-tris(isopropoxy-κ1O trititanium(IV)), C48H55N2O13Fe2Ti3
  8. Crystal structure of 3-(diethylamino)-7,9,11-trimethyl-8-phenyl-6H,13H-12λ4,13λ4-chromeno[3′,4′:4,5]pyrrolo[1,2-c]pyrrolo[2,1-f][1,3,2]diazaborinin-6-one, C28H26BF2N3O2
  9. The crystal structure of catena-poly[aqua-μ2-2-nitro-benzene-1,3-dicarboxylato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)-zinc(II)], C20H13N3O7Zn
  10. Crystal structure of poly[diaqua-{μ3-1-(3-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ4O,O′:O′′:O′′′′}manganese(II)] hydrate
  11. Crystal structure of N′-((1-hydroxycyclohexyl)(phenyl)methyl)-2-methoxybenzohydrazide methanol solvate, C22H28N2O4
  12. The cocrystal of caffeic acid — progesterone — water (1/2/1), C51H70O9
  13. Crystal structure of (((oxido(quinolin-6-yl)methoxy)triphenyl-λ5-stibanyl)oxy)(quinolin-7-yl)methanolate
  14. Crystal structure of [(E)-6′-(diethylamino)-2-(2-(((E)-pyren-1-ylmethylene)amino)ethyl)-4′-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)-1′,2′,3′,4′-tetrahydrospiro[isoindoline-1,9′-xanthen]-3-one]-methanol, solvate C57H56N4O3
  15. The crystal structure of 1-(acridin-9-yl)pyrrolidine-2,5-dione, C17H22N2O2
  16. Crystal structure of N-(4-acetylphenyl)-2-(6-methoxynaphthalen-2-yl)propanamide, C22H21NO3
  17. The crystal structure of 5,10,15,20-tetrakis(4-(1H-1,2,4-triazol-1-yl)phenyl)porphyrin, C52H34N16
  18. Crystal structure of hexacarbonyl-μ2-[phenylmethanedithiolato-κ4S:S,S′:S′]diiron (Fe–Fe) C13H6Fe2O6S2
  19. Crystal structure of diiodo-bis(1-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ1N)cadmium(II), C34H34CdI2N10
  20. Crystal structure of (E)-(3-(3-bromophenyl)acryloyl)ferrocene, C19H15BrFeO
  21. Crystal structure of catena-poly(μ2-6-chloropyridine-2-carboxylato-κ3N,O:O′)(6-chloropyridine-2-carboxylato-κ2O,N)copper(II), C12H6Cl2N2O4Cu
  22. Crystal structure of poly[diaqua-μ 3-(5-(3,5-dicarboxy-2,4,6-trimethylbenzyl)-2,4,6-trimethylisophthalato)-κ 6O,O′:O″,O‴:O‴′,O‴″) terbium(III)-monohydrate], C23H28TbO12
  23. Crystal structure of (E)-2-(((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one – ethanol (1/2), C35H33ClN4O6
  24. The crystal structure of 3-(5-amino-3-phenylisoxazol-4-yl)-4-chloro-3-hydroxyindolin-2-one, C17H12ClN3O3
  25. The crystal structure of dimethylammonium 4-[2-(4-fluorophenyl)-4, 5-diphenyl-1H-imidazol-1-yl]benzenesulfonate, C29H26FN3O3S
  26. Crystal structure of (R)-2-ammonio-3-((5-carboxypentyl)thio)propanoate
  27. Crystal structure of 4-cyclohexyl-5-(thiophen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C12H15N3S2
  28. The crystal structure of 4,6-bis(dimethylamino)-2-fluoroisophthalonitrile, C12H13FN4
  29. Hydrogen bonding in the crystal structure of nicotin-1,1′-dium tetrabromidomanganate(II)
  30. The crystal structure of bis(2-bromobenzyl)(2-((2-oxybenzylidene)amino)-4-methylpentanoato-κ3N, O,O′)tin(IV), C27H27Br2NO3Sn
  31. Crystal structure of (E)-(3-(p-tolyl)acryloyl)ferrocene, C20H18FeO
  32. Crystal structure of (E)-7-fluoro-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C21H22FN3O
  33. Crystal structure of (E)-7-methoxy-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C22H25N3O2
  34. The crystal structure of poly(bis(μ2-1,3,5-tri(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-2,3,5,6-tetrafluoroterephthalato-κ2O:O′)-manganese(II), C38H24F4N12O4Mn
  35. Crystal structure of (3,4-dimethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO3P
  36. Crystal structure of tetraethylammonium hydrogencarbonate – (diaminomethylene)thiourea – water (2/1/3)
  37. Crystal structure of N, N-Dimethyl-N′-tosylformimidamide, C10H14N2O2S
  38. The crystal structure of ethyl 2-methyl-5-oxo-4-(2-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H23N2O4
  39. Crystal structure of bis(μ2-1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene] thiocarbonohydrazide)-bis(dimethylformamide)-dizinc(II) dimethylformamide solvate, C40H46N10O6S2Zn2⋅C3H7NO
  40. Crystal structure of azido-κ1N{hydridotris(3-tert-butyl-5-methylpyrazol-1-yl)borato-κ3N,N′,N″}copper(II), C24H40BCuN9
  41. The crystal structure of fac-tricarbonyl(1,10-phenanthroline-κ2N,N′)-(azido-κ1N)rhenium(I), C15H8N5O3Re
  42. Crystal structure of 4-((triphenylphosphonio)methyl)pyridin-1-ium tetrachloridozincate(II), C24H22Cl4NPZn
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