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Chemical Structure| 102664-66-4 Chemical Structure| 102664-66-4

Structure of 102664-66-4

Chemical Structure| 102664-66-4

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Product Details of [ 102664-66-4 ]

CAS No. :102664-66-4
Formula : C24H21N3
M.W : 351.44
SMILES Code : C1(NC2=CC=CC=C2)=CC(NC3=CC=CC=C3)=CC(NC4=CC=CC=C4)=C1
MDL No. :MFCD01463903
InChI Key :BMQHYGLEATWRFO-UHFFFAOYSA-N
Pubchem ID :227820

Safety of [ 102664-66-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 102664-66-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 27
Num. arom. heavy atoms 24
Fraction Csp3 0.0
Num. rotatable bonds 6
Num. H-bond acceptors 0.0
Num. H-bond donors 3.0
Molar Refractivity 115.07
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

36.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.35
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

6.55
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

6.92
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

5.0
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.27
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.22

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-6.41
Solubility 0.000138 mg/ml ; 0.000000392 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-7.11
Solubility 0.0000275 mg/ml ; 0.0000000783 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-10.06
Solubility 0.0000000305 mg/ml ; 0.0000000001 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-3.79 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.05

Application In Synthesis of [ 102664-66-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 102664-66-4 ]

[ 102664-66-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 102664-66-4 ]
  • <i>N</i>1,<i>N</i>3,<i>N</i>5-trinitroso-<i>N</i>1,<i>N</i>3,<i>N</i>5-triphenyl-benzene-1,3,5-triyltriamine [ No CAS ]
  • 2
  • [ 102664-66-4 ]
  • [ 108-24-7 ]
  • <i>N</i>,<i>N</i>',<i>N</i>''-benzene-1,3,5-triyl-tris-acetanilide [ No CAS ]
  • 3
  • [ 102664-66-4 ]
  • [ 98-88-4 ]
  • <i>N</i>,<i>N</i>',<i>N</i>''-benzene-1,3,5-triyl-tris-benzanilide [ No CAS ]
  • 5
  • [ 871877-82-6 ]
  • [ 62-53-3 ]
  • [ 102664-66-4 ]
  • 6
  • [ 716306-63-7 ]
  • [ 62-53-3 ]
  • [ 102664-66-4 ]
  • 8
  • [ 615-37-2 ]
  • [ 102664-66-4 ]
  • 1,3,5-Tris(2-methylphenylphenylamino)benzene [ No CAS ]
  • 11
  • [ 102664-66-4 ]
  • [ 104-15-4 ]
  • C24H22N3(1+)*C7H7O3S(1-) [ No CAS ]
  • 12
  • [ 3437-95-4 ]
  • [ 102664-66-4 ]
  • 1,3,5-tris(phenyl-2-thienylamino)benzene [ No CAS ]
  • 13
  • [ 10486-61-0 ]
  • [ 102664-66-4 ]
  • 1,3,5-tris(phenyl-3-thienylamino)benzene [ No CAS ]
  • 14
  • [ 637-87-6 ]
  • [ 102664-66-4 ]
  • N,N',N''-Tris-(4-chloro-phenyl)-N,N',N''-triphenyl-benzene-1,3,5-triamine [ No CAS ]
  • 15
  • [ 352-34-1 ]
  • [ 102664-66-4 ]
  • N,N',N''-Tris-(4-fluoro-phenyl)-N,N',N''-triphenyl-benzene-1,3,5-triamine [ No CAS ]
  • 16
  • [ 589-87-7 ]
  • [ 102664-66-4 ]
  • 1,3,5-tris((4-bromophenyl)phenylamino)benzene [ No CAS ]
  • 17
  • [ 102664-66-4 ]
  • 2-Nitroso-N,N',N''-triphenyl-benzene-1,3,5-triamine [ No CAS ]
  • 18
  • [ 102664-66-4 ]
  • 2,4,6-tris(phenylamino)[15N]nitrosobenzene [ No CAS ]
  • 19
  • [ 38257-52-2 ]
  • [ 102664-66-4 ]
  • 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene [ No CAS ]
  • 20
  • [ 108-73-6 ]
  • [ 62-53-3 ]
  • CaCl2 [ No CAS ]
  • [ 102664-66-4 ]
  • 21
  • [ 4214-28-2 ]
  • [ 102664-66-4 ]
  • 1,3,5-Tris[(2,4-dimethylphenyl)phenylamino]benzene [ No CAS ]
  • 22
  • [ 625-99-0 ]
  • [ 102664-66-4 ]
  • 1,3,5-Tris[(3-chlorophenyl)phenylamino]benzene [ No CAS ]
  • 23
  • [ 31599-61-8 ]
  • [ 102664-66-4 ]
  • 1,3,5-Tris[(3,4-dimethylphenyl)phenylamino]benzene [ No CAS ]
  • 24
  • [ 22445-41-6 ]
  • [ 102664-66-4 ]
  • 1,3,5-Tris[(3,5-dimethylphenyl)phenylamino]benzene [ No CAS ]
  • 26
  • [ 589-87-7 ]
  • [ 102664-66-4 ]
  • <i>N</i>,<i>N</i>',<i>N</i>''-tris-(4'-bromo-biphenyl-4-yl)-benzene-1,3,5-triamine [ No CAS ]
  • 27
  • [ 716306-63-7 ]
  • [ 102664-66-4 ]
  • 28
  • [ 106-37-6 ]
  • [ 102664-66-4 ]
  • 1,3,5-tris((4-bromophenyl)phenylamino)benzene [ No CAS ]
  • 29
  • [ 102664-66-4 ]
  • [ 101-54-2 ]
  • 1,3,7-tris(phenylamino)-5-phenylphenazinium sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With potassium dichromate; sulfuric acid; In water; acetone; at 40 - 50℃; for 1h; Amixture of 1,3,5-tris(phenylamino)benzene 9 (382 mg, 1.10 mmol)and N-phenyl-p-phenylenediamine (200 mg, 1.10 mmol) in water andacetone (150 mL/100 mL) with cH2SO4 (6 drops, 0.3 mL) were treatedwith K2Cr2O7 (320 mg, 1.10 mmol) and heated at 40-50 C for 1 hwith stirring in a beaker covered with a petri dish. The petri dish wasthen removed and heating and stirring continued for a further 2-3 hto evaporate the acetone. The acetone must be evaporated before themixture is filtered. After allowing to cool the mixture was filteredthrough a fine pore sinter and washed with H2O. The precipitate wasextracted with MeOH (6 × 50 mL) in the sinter each time agitatingthe precipitate. The combined MeOH extracts were evaporated to dryness then purified by chromatography on silica gel. After elutionwith MeOH, elution with cNH3/MeOH (20/80) gave the title compound(198 mg, 34%) as a dark blue solid
  • 30
  • [ 102664-66-4 ]
  • [ 106-50-3 ]
  • 1,3-bis(phenylamino)-5-phenyl-7-amino-phenazinium sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With potassium dichromate; sulfuric acid; In water; acetone; at 40 - 50℃; for 1h; A mixture of1,3,5-tris(phenylamino)benzene 95 (382 mg, 1.10 mmol) andp-phenylenediamine (118 mg, 1.10 mmol) in water and acetone(150 mL/100 mL) with cH2SO4 (six drops, 0.3 mL) was treated withK2Cr2O7 (320 mg, 1.10 mmol) and heated at 40-50 C for 1 h withstirring in a beaker covered with a petri dish. The petri dish was thenremoved and heating and stirring continued for a further 2-3 h toevaporate the acetone. The acetone must be evaporated before themixture is filtered. After allowing the mixture to cool it was filteredthrough a fine pore sinter and washed with H2O. The precipitate wasextracted with MeOH (6 × 50 mL) in the sinter each time agitatingthe precipitate. The combined MeOH extracts were evaporated todryness then purified by chromatography on silica gel. After elutionwith MeOH elution with cNH3/MeOH (20/80) gave the title compound(194 mg, 35%) as a dark purple glistening solid,
  • 31
  • [ 156-10-5 ]
  • [ 102664-66-4 ]
  • [ 1636889-27-4 ]
YieldReaction ConditionsOperation in experiment
18% With hydrogenchloride; In ethanol; water; for 3h; 1,3,5-tris(Phenylamino)benzene 9 (100 mg, 0.285 mmol) and4-nitrosodiphenylamine 12 (56 mg, 0.285 mmol) in EtOH (10 mL) andcHCl (5 mL) were heated to dryness in a beaker over 3 h in a fume hood.After the addition of water the product was filtered off and purifiedby chromatography on silica gel. MeOH eluted the title compound(23 mg, 18%) as a dark green solid
  • 32
  • [ 156-10-5 ]
  • [ 102664-66-4 ]
  • [ 1636889-27-4 ]
  • 1,3,7-tris(phenylamino)-5-phenylphenazinium sulfate [ No CAS ]
  • 33
  • [ 626-39-1 ]
  • [ 62-53-3 ]
  • [ 102664-66-4 ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 72h;Inert atmosphere; Reflux; A mixture of aniline (7.4 g, 79.4 mmol), 1,3,5-tribromobenzene 3 (5.0 g, 15.88 mmol), tris(dibenzylideneacetone) dipalladium(0) [Pd2(dba)3(0), 0.11 g, 0.25 mol %], rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.22 g, 0.75 mol %), and sodium t-butoxide (7.63 g, 79.4 mmol) in anhydrous toluene (250 mL) was heated to refluxing temperature under nitrogen for a period of 72 h. The reaction mixture was cooled to room temperature and washed with water (100 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4). After evaporation of the solvent, a crude brown color solid was obtained. Excess aniline was then removed by distillation at 130 C under reduced pressure of 101 mmHg. It was further purified by chromatography (SiO2). The resulting light brown product 1,3,5-tris(phenylamino)benzene 4, TPAB, was obtained in 75% yield (4.18 g). FT-IR (KBr) upsilonmax 3403 (m), 3375 (m), 3078 (w), 3019 (w), 2945 (s), 1612 (m), 1591 (vs), 1518 (m), 1496 (s), 1469 (m), 1431(w), 1456 (m), 1409 (m), 1365 (w), 1295 (m), 1269 (w), 1246 (m), 1,171 (m), 1073 (w), 1030 (w), 897 (w), 834 (w), 820 (w), 802 (w), 756 (m), 721 (w), 700 (m), 688 (m), 613 (w), and 558 (w) cm-1; UV-vis (CHCl3, 1.0 × 10-5 M) lambdamax (epsilon) 289 nm (4.80 × 104 L mol-1 cm-1); 1H-NMR (500 MHz, CDCl3) delta 7.25 (t, J = 7.8 Hz, 6H), 7.08 (d, J = 7.7 Hz, 6H), 6.92 (t, J = 7.3 Hz, 3H), 6.32 (s, 3H), and 5.60 (s, 3H, N-H); 13C-NMR (125 MHz, CDCl3) delta 145.4, 142.7, 129.3, 121.3, 118.7, and 99.0.
  • 34
  • [ 887951-49-7 ]
  • [ 102664-66-4 ]
  • N1,N3,N5-tris(9,9-di(3,,5,,5,-trimethyl-1,-hexyl)fluoren-2-yl)-1”,3”,5”-tris(phenylamino)benzene, [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 72h;Inert atmosphere; Reflux; A mixture of 2-bromo-9,9-bis(3',5',5'-trimethyl-1'-hexyl)fluorene (8.39 g, 17.04 mmol, excess), <strong>[102664-66-4]1,3,5-tris(N-phenylamino)benzene</strong> (1.0 g, 2.84 mmol), tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3(0), 0.02 g, 0.25 mol %], rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.04 g, 0.75 mol %), and sodium t-butoxide (1.63 g, 17.04 mmol) in anhydrous toluene (75 mL) was heated to refluxing temperature under nitrogen for a period of 72 h. The reaction mixture was cooled to room temperature and washed with water (50 mL). The organic layer was dried over anhydrous sodium sulfate. After evaporation of the solvent, it afforded a crude brown colored paste. The paste was subjected to column chromatography purification using silica gel as the stationary phase and hexane-ethyl acetate(9:1) as the eluent, to afford N1,N3,N5-tris(9,9-di(3',5',5'-trimethyl-1'-hexyl)fluoren-2-yl)-1",3",5"-tris(phenylamino)-benzene, tris(DPAF-C9) 7, as light yellow solids or clear thick sticky gel-like paste, while residual solvents are present, in 88% yield (3.98 g). FT-IR (KBr) upsilonmax 3,063 (w, aromatic C-H stretching), 3,037 (w), 3,019 (w), 2,953 (vs, aliphatic C-H stretching), 2,865 (s), 1,583 (s, C=C), 1500 (s), 1,493 (s, anti-symmetric deformations of CH3 groups and scissor vibrations of CH2 groups), 1,450, 1392 (w), 1363 (m, symmetric deformations of CH3 groups), 1294 (m, asymmetric stretching vibrations of C-N-C), 1249 (w, asymmetric stretching vibrations of C-N-C), 1212 (w), 1178 (w), 1155 (w), 1037 (w), 1006 (w), 933 (w), 878 (w), 826 (w), 756 (w), 738 (s, C-H out-of-plan deformation), 711 (m, C-H out-of-plan deformation), 693 (m), 628 (w), and 510 (w) cm-1; UV-vis (CHCl3, 1.0 × 10-5 M) lambdamax (epsilon) 323 (5.71 × 104) and 348 nm (5.66 × 104 L mol-1 cm-1); PL (CHCl3,1.0 × 10-5 M) lambdaem,max 390.1 nm; 1H-NMR (500 MHz, CDCl3) delta 7.57 (s, 3H, br), 7.51 (d, J = 7.5 Hz, 3H), 7.32-7.21 (m, 9H), 7.09-7.01 (m, 18H), 6.82 (t, J = 7.2 Hz, 3H), 6.55 (s, 3H, br), 1.92-1.67 (m, 12H), 1.11 (s, 6H), and 0.97-0.39 (m, 96H); 13C-NMR (125 MHz, CDCl3) delta 151.9, 150.4, 149.3, 147.6, 146.5, 141.0, 136.5, 128.9, 126.7, 126.3, 123.7, 122.7, 121.9, 120.2, 119.1, 115.6, 54.7, 50.9, 50.63, 50.57, 38.0, 37.9, 37.6, 37.5, 33.1, 32.8, 30.9, 30.0, 29.5, 29.3, 27.3, 22.7, and 22.5; MALDI-TOF MS calcd for C117H153N3, m/z 1600.2; found, m/z 1601.6 (MH+).
83% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 72h;Reflux; Inert atmosphere; Synthetic procedure of tris(DPAF-C9) was followed by and slightly modified from the recently reported methods [22]. A typical procedure was given as follows. A mixture of BrF-C9 (10.0 g,20.3 mmol, excess), TPAB (1.16 g, 3.30 mmol), Pd2(dba)3(0) (0.023 g, 0.25 mol%), BINAP (0.046 g,0.75 mol%), and sodium t-butoxide (1.94 g, 20.3 mmol) taken in anhydrous toluene (75 mL) was heated to refluxing temperature under nitrogen for a period of 72 h. After being cooled to roomtemperature, the reaction mixture was washed with water for three times and dried over sodium sulfate. A crude brown colored paste was obtained after evaporating the solvent. It was subjected to column chromatography purification using silica gel as the stationary phase and hexane-ethylacetate(9:1) as the eluent. The product of tris(DPAF-C9) was collected at Rf = 0.8 as light yellow solids in 83%yield (4.35 g).
  • 35
  • [ 887951-49-7 ]
  • [ 102664-66-4 ]
  • N1,N3-bis(9,9-di(3',5',5'-trimethyl-1'-hexyl)fluoren-2-yl)-1",3",5"-tris(phenylamino)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; for 72h;Inert atmosphere; Reflux; A mixture of 2-bromo-9,9-bis(3',5',5'-trimethyl-1'-hexyl)fluorene (0.71 g, 1.42 mmol), 1,3,5-tris(phenylamino)benzene (0.25 g, 0.71 mmol), tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3(0), 0.005 g, 0.25 mol %], rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.01 g, 0.75 mol %), and sodium t-butoxide (0.70 g, 7.10 mmol) in anhydrous toluene (50 mL) was heated to refluxing temperature under nitrogen for 72 h. The reaction mixture was cooled to room temperature and washed with water (30 mL). The organic layer was dried over anhydrous sodium sulfate. After evaporation of the solvent, it afforded a crude brown colored semi-solid. It was purified by column chromatography using silica gel as the stationary phase and hexane-ethylacetate (9:1) as the eluent to afford N1,N3-bis(9,9-di(3',5',5'-trimethyl-1'-hexyl)fluoren-2-yl)-1",3",5"-tris(phenylamino)benzene, bis(DPAF-C9) 6, as whiteto light yellow glassy solids in 52% yield (0.43 g). FT-IR (KBr) upsilonmax 3402 (m), 3062 (w), 3036 (w), 3010 (w), 2953 (s), 2865 (m), 1585 (s), 1492 (s), 1467 (m), 1450 (m), 1,422 (w), 1392 (m), 1363 (w), 1299 (m), 1252 (m), 1213 (w), 1155 (w), 1079 (w), 1033 (w), 824 (w), 738 (m), 711 (w), 693 (m), and 512 (w) cm-1;UV-vis (CHCl3, 1.0 × 10-5 M) lambdamax (epsilon) 308 (5.56 × 104) and 348 nm (5.07 × 104 L mol-1 cm-1); PL (CHCl3,1.0 × 10-5 M) lambdaem,max 390.8 nm; 1H-NMR (500 MHz, CDCl3) delta 7.61-7.58 (m, 4H), 7.34-7.21 (m, 7H), 7.16(t, J = 7.2 Hz, 4H), 7.12-7.01 (m, 10H), 6.90 (t, J = 6.8 Hz, 1H), 6.86-6.83 (m, 2H), 6.74 (t, J = 6.5 Hz, 1H), 6.53 (s, 1H), 6.42 (s, 2H), 5.51 (s, 1H), 1.98-1.71 (m, 8H), 1.21-1.07 (s, 4H, br), 0.97-0.86 (d, 4H), and ,0.83-0.34 (m, 60H); 13C-NMR (125 MHz, CDCl3) delta 151.9, 150.5, 149.6, 147.8, 146.7, 142.5, 141.0, 136.6, 129.1, 129.0, 126.7, 126.3, 124.1, 123.1, 122.7, 122.0, 120.6, 120.2, 119.1, 117.2, 112.8, 108.10, 108.0, 100.0, 54.8, 50.9, 50.7, 38.0, 37.9, 37.7, 37.6, 33.1, 32.9, 30.9, 29.9, 29.5, 29.30, 29.27, 27.3, 22.6, and 22.5; MALDI-TOF MS calcd for C86H109N3, m/z 1,183.9; found, m/z 1,184.9 (MH+).
 

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