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Reaction 16: Bidirectional Sonogashira Coupling: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
30th July 2013 @ 14:55

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SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Francesco Giustiniano   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conceiver
Author 4          

TEXT

*Procedure or Transformation Bidirectional Sonogashira Coupling
*Compound(s) being made 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
*Chemicals used (delimited by semicolons ;) 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene;  4-bromobenzonitrile; PdCl2; PPh3; CuI; benzene; Triethylamine
*Procedure A small Schlenk tube containing 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene(40 mg, 46 μmol), 4-bromobenzonitrile (20 mg, 0.11 mmol, 2.40 eq.), PdCl2 (1 mg, 5.00 μmol, 10 mol%), PPh3 (3 mg, 0.01 mmol, 20 mol%) and CuI (2 mg, 0.01 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding benzene (1.0 mL: ~ 20 mL/mmol) and triethylamine, TEA (0.04 mL, 28 mg, 0.28 mmol, 6.00 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 22 h. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude product (mostly yellow solid, 91 mg). The pure title compound (Rf 0.36; yellow solid, 18 mg, 17 μmol, yield 37%) was obtained by column chromatography on silica gel using as eluent (2/1) DCM/hexane.
*Authors Comments

Similar approach has been taken: 

Using 1-(2-(2,5-Didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene as starting material and distilled benzene (in step ii) afforded 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-cyanophenyl)ethynyl)phenyl)ethynyl) benzene in 41% yield. 
Lead Reference Taken from: F. Giustiniano, 2010, "Directed Assembly of Functional Patterns",PhD thesis, University of Southampton. Pages 13, 114
Other References  
Multimedia Content  
*Data 1H NMR (400 MHz, CDCl3, D1 5 s); 13C NMR (100 MHz, CDCl3, NS 6144)
#Data file 1
H NMR 16 - ju1606fg1 .jdx
#Data file 2
C NMR 16 - ju1606fg1 .jdx
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
reactionscheme_16 .cdx
*#Image file (GIF or PNG)
reactionscheme_16 .gif

Keywords

Compounds Keywords Aromatics; alkynes
Reactions Keywords substitution
Other Keywords  
Attached Files
Lee Y.W. (ywl1g11) | View Source | F. Giustiniano | Comments (0)
Compound 16: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
30th July 2013 @ 14:53

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Compound

ChemSpider ID 29289767
*#Name of Compound mol file
1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene.mol

Description and Tags

Description  
Tags (separated by comma)  

Identifiers

*Chemical Name 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
Common Name  
Synonym  

Spectra

  *#Spectrum jcamp file *Spectrum Type Comments OpenData Image or PDF
Spectrum 1
H NMR 16 - ju1606fg1 .jdx
 H NMR 1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.63 (8H, m, Ar4), 7.54-7.52 (16H, m, Ar3-Ar2), 7.37 (2H, s, Ar1), 2.81 (4H, t, J = 7.8, C1), 1.71 (4H, pent J = 7.4, C2), 1.43-1.25 (36H, m, C3-C11), 0.87 (6H, t, J = 6.9, C12) Y
H NMR 16 .pdf
Spectrum 2
C NMR 16 - ju1606fg1 .jdx
 C NMR 13C NMR (100 MHz, CDCl3, NS 6144): δ 142.75 (C, Ar1R), 132.77, 132.45 (double intensity), 132.12, 132.02, 131.99, 131.81 (7CH, Ar1-Ar2-Ar3-Ar4), 128.32 (C, Ar4CC), 124.21, 124.04, 123.05, 122.90, 122.53 (5C, CCAr3CCAr2-CCAr1), 118.80 (C, Ar4CN), 112.11 (C, Ar4CN), 94.09, 93.71, 91.90, 91.12, 90.97, 89.93 (6C, Ar4CCAr3CCAr2CCAr1), 34.49 (CH2, C1), 32.29 (CH2, C10), 31.03 (CH2, C2),  30.06-29.71 (7CH2, C3-C9), 23.05 (CH2, C11), 14.46 (CH3, C12) Y
C NMR 16 .pdf
Spectrum 3
C NMR DEPT135 - 16 - ju1606fg1 .jdx
 C NMR DEPT 135  Y
C NMR DEPT135 - 16 .pdf
Spectrum 4   MALDI-TOF LRMS (MALDI-TOF): m/z 1065 ([M+], 100 %)  Y
16-MALDI.JPG
Spectrum 5   Infrared IR (film): 2921, 2848 (m, CH stretch), 2357, 2337 (m, CC stretch, alkyne) Y
16-IR.JPG
Spectrum 6          
Spectrum 7          
Spectrum 8          
Spectrum 9          
Spectrum 10          

Properties

Experimental Physico-chemical Properties

Property Value Unit Comments
Experimental Boiling Point      
Experimental Flash Point      
Experimental Freezing Point      
Experimental Gravity      
Experimental Ionization Potent      
Experimental LogP      
Experimental Melting Point 168 °C  
Experimental Optical Rotation      
Experimental Refraction Index      
Experimental Solubility      
Experimental Vapor Pressure      
Non Water Solubility      
Non Water Solubility      

Spectroscopy

Property Value Unit Comments
Lambda Max 373 nm (CHCl3); (ε 61000)

Miscellaneous

Property Value Unit Comments
Appearance Yellow Solid    
Bio Activity      
Chemical Class      
Compound Source      
Drug Status      
Exposure Limits      
Exposure Limits Niosh Rel      
Exposure Routes      
First-Aid      
Incompatability      
Personal Protection      
Safety      
Stability      
Symptoms      
Target Organs      
Therapeutical Effect      
Toxicity      
Attached Files
Lee Y.W. (ywl1g11) | View Source | F. Giustiniano | Comments (0)
Reaction 15: Deprotection of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene
30th July 2013 @ 14:18

This post is compatible for submission to ChemSpider SyntheticPages.

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SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Francesco Giustiniano   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conceiver
Author 4          

TEXT

*Procedure or Transformation Deprotection of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
*Compound(s) being made 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene
*Chemicals used (delimited by semicolons ;) 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene; THF; TBAF
*Procedure In a 50 mL rbf a solution of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene(58 mg, 0.06 mmol) in THF (10 mL: large excess) was stirred for 15 min, at r.t., in presence of TBAF (0.84 mL of a solution 1 M in THF; 14.00 eq.); the disappearance of starting material (Rf 0.00, (20/1) hexane/DCM) was monitored by TLC. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine, dried over anhydrous MgSO4 and evaporated, to afford the crude product (bright yellow solid, 56 mg, 0.06 mmol, yield 93%). No further purification was carried out. 
*Authors Comments The deprotection with K2CO3 and methanol/DCM was not viable because of the too low solubility of the starting material in methanol/DCM.
Lead Reference Taken from: F. Giustiniano, 2010, "Directed Assembly of Functional Patterns",PhD thesis, University of Southampton. Pages 13, 113
Other References  
Multimedia Content  
*Data 1H NMR (400 MHz, CDCl3, D1 5 s); 13C NMR (100 MHz, CDCl3, NS 3072)
#Data file 1
H NMR 15 - fe1506sd2 .jdx
#Data file 2
C NMR 15 - fe1506sd2 .jdx
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
reactionscheme_15 .cdx
*#Image file (GIF or PNG)
reactionscheme_15 .gif

Keywords

Compounds Keywords Aromatics; alkynes
Reactions Keywords substitution
Other Keywords  
Attached Files
Lee Y.W. (ywl1g11) | View Source | F. Giustiniano | Comments (0)
Compound 15: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene
30th July 2013 @ 14:18

This post is compatible for submission to ChemSpider.

See ChemSpider compound and associated data template - help and further information for help when using it.

Compound

ChemSpider ID 29289769
*#Name of Compound mol file
1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene .mol

Description and Tags

Description  
Tags (separated by comma)  

Identifiers

*Chemical Name 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene
Common Name  
Synonym  

Spectra

  *#Spectrum jcamp file *Spectrum Type Comments OpenData Image or PDF
Spectrum 1
H NMR 15 - fe1506sd2 .jdx
 H NMR 1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.51 (8H, m, Ar3), 7.48 (8H, m, Ar2), 7.37 (2H, s, Ar1), 3.18 (2H, s, CCH), 2.81 (4H, t, J = 7.8, C1), 1.70 (4H, pent, J = 7.5, C2), 1.42-1.23 (36H, m, C3-C11), 0.87 (6H, t, J = 6.8, C12) Y
H NMR 15 .pdf
Spectrum 2  
C NMR 15 - fe1506sd2 .jdx
 C NMR 13C NMR (100 MHz, CDCl3, NS 3072): δ 142.54 (C, Ar1R), 132.56, 132.27, 131.78, 131.64, 131.59 (5CH, Ar3-Ar2-Ar1), 123.75, 123.70, 122.92, 122.70, 122.28 (5C, Ar1CCAr2CCAr3CCH), 93.89, 91.25, 90.89, 90.70 (4C, Ar3CCAr2CCAr1), 83.39 (C, Ar3CCH), 79.18 (CH, Ar3CCH; low intensity in DEPT), 34.29 (CH2, C1), 32.10 (CH2, C10), 30.83 (CH2, C2), 29.86-29.52 (7CH2, C3-C9), 22.85 (CH2, C11), 14.26 (CH3, C12) Y
C NMR 15 .pdf
Spectrum 3
C NMR DEPT135 15 - fe1506sd2 .jdx
 C NMR DEPT 135 Y
C NMR DEPT135 - 15 .pdf
Spectrum 4   MALDI-TOF LRMS (MALDI-TOF, DHB): m/z 862 ([M+], 100) Y
15-MALDI.JPG
Spectrum 5   Infrared  IR (film): 3290 (w, CH stretch, alkyne), 2958 (w), 2918, 2853 (m, CH stretch) Y
15-IR.JPG
Spectrum 6          
Spectrum 7          
Spectrum 8          
Spectrum 9          
Spectrum 10          

Properties

Experimental Physico-chemical Properties

Property Value Unit Comments
Experimental Boiling Point      
Experimental Flash Point      
Experimental Freezing Point      
Experimental Gravity      
Experimental Ionization Potent      
Experimental LogP      
Experimental Melting Point 115-120 °C  
Experimental Optical Rotation      
Experimental Refraction Index      
Experimental Solubility      
Experimental Vapor Pressure      
Non Water Solubility      
Non Water Solubility      

Spectroscopy

Property Value Unit Comments
Lambda Max 361 nm (CHCl3); (ε 70600)

Miscellaneous

Property Value Unit Comments
Appearance bright yellow solid    
Bio Activity      
Chemical Class      
Compound Source      
Drug Status      
Exposure Limits      
Exposure Limits Niosh Rel      
Exposure Routes      
First-Aid      
Incompatability      
Personal Protection      
Safety      
Stability      
Symptoms      
Target Organs      
Therapeutical Effect      
Toxicity      
Attached Files
Lee Y.W. (ywl1g11) | View Source | F. Giustiniano | Comments (0)
Compound 14: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
30th July 2013 @ 11:51

This post is compatible for submission to ChemSpider.

See ChemSpider compound and associated data template - help and further information for help when using it.

Compound

ChemSpider ID 29289433
*#Name of Compound mol file
1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene .mol

Description and Tags

Description  
Tags (separated by comma)  

Identifiers

*Chemical Name 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
Common Name  
Synonym  

Spectra

  *#Spectrum jcamp file *Spectrum Type Comments OpenData Image or PDF
Spectrum 1
H NMR 14 - fe1106sd1 .jdx
 H NMR   1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.50 (8H, m, Ar3), 7.45 (8H, m, Ar2), 7.37 (2H, s, Ar1), 2.81 (4H, t, J = 7.8, C1), 1.70 (4H, pent, J = 7.5, C2), 1.43-1.25 (36H, m, C3-C11), 0.87 (6H, t, J = 6.9, C12), 0.26 (18H, s, TMS). Y
H NMR - 14 .pdf
Spectrum 2
C NMR - 14 - fe1106sd1 .jdx
 C NMR  13C NMR (100 MHz, CDCl3, NS 3072): δ 142.54 (C, Ar1R), 132.55, 132.09, 131.75, 131.58, 131.56 (5CH, Ar1-Ar2-Ar3), 123.68, 123.32, 123.25, 123.00, 122.70 (5C, Ar1CCAr2CCAr3CC), 104.75 (C, TMSCCAr3), 96.62 (C, TMSCC), 93.90, 91.18, 91.11, 90.67 (4C, Ar3CCAr2CCAr1), 34.29 (CH2, C1), 32.09 (CH2, C10), 30.83 (CH2, C2), 29.85-29.53 (7CH2, C3-C9), 22.85 (CH2, C11; not visible in DEPT), 14.26 (CH3, C12), 0.07 (CH3, TMS) Y
C NMR 14 .pdf
Spectrum 3
C NMR DEPT135 - 14 - fe1106sd1 .jdx
 C NMR   DEPT 135 Y
C NMR DEPT135 - 14 .pdf
Spectrum 4   MALDI-TOF LRMS (MALDI-TOF, alpha): m/z 1008 ([M+H]+, 100), 885 (13), 699 (16) Y 
14-MALDI.JPG
Spectrum 5   Infrared IR (film): 2950 (w), 2919 (m), 2851 (w, CH stretch), 2154 (w, CC stretch, alkyne) Y 
14-IR.JPG
Spectrum 6          
Spectrum 7          
Spectrum 8          
Spectrum 9          
Spectrum 10          

Properties

Experimental Physico-chemical Properties

Property Value Unit Comments
Experimental Boiling Point      
Experimental Flash Point      
Experimental Freezing Point      
Experimental Gravity      
Experimental Ionization Potent      
Experimental LogP      
Experimental Melting Point 168-171 °C    
Experimental Optical Rotation      
Experimental Refraction Index      
Experimental Solubility      
Experimental Vapor Pressure      
Non Water Solubility      
Non Water Solubility      

Spectroscopy

Property Value Unit Comments
Lambda Max      

Miscellaneous

Property Value Unit Comments
Appearance White Solid     
Bio Activity      
Chemical Class      
Compound Source      
Drug Status      
Exposure Limits      
Exposure Limits Niosh Rel      
Exposure Routes      
First-Aid      
Incompatability      
Personal Protection      
Safety      
Stability      
Symptoms      
Target Organs      
Therapeutical Effect      
Toxicity      
Attached Files
Lee Y.W. (ywl1g11) | View Source | F. Giustiniano | Comments (0)
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