2-(4-bromophenyl)-3,3-diphenylprop-2-enenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A related material was prepared in which the vinylic hydrogen of C(DPVBi)4 is substituted with a cyano group. The stabilized LUMO of the cyano-substituted triphenylethene fragment (2,3,3-triphenylacrylonitrile) is expected to enhance electron injection and transport as is observed for CN-PPV.38 Knovenagle condensation between 4-bromobenzonitrile and benzophenone gives 2-(4-bromophenyl)-3,3-diphenylacrylonitrile (Scheme 4). Metathesis of the bromine atom for boronpinacolate proceeds in good yield using the method of Miyaura.39 In this case metathesis of bromine using the n-BuLi/B(OiPr)3 protocol is not compatible with the sensitive cyano functionality. Five equivalents of 2-(4-pinacolatoboron-phenyl)-3,3-diphenylacrylonitrile react smoothly with tetrakis(4-bromophenyl)methane using the optimized Pd(dppf)Cl2 catalyzed coupling conditions to yield tetrakis(4,4′-(3,3-diphenylacrylonitrile)-1,1′-biphenyl)methane, C(DPAB)4 in 82% yield, following purification by flash chromatography. Compound C(DPAB)4 has been fully characterized and the details can be found in the Examples.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A related material was prepared in which the vinylic hydrogen of C(DPVBi)4 is substituted with a cyano group. The stabilized LUMO of the cyano-substituted triphenylethene fragment (2,3,3-triphenylacrylonitrile) is expected to enhance electron injection and transport as is observed for CN-PPV.38 Knovenagle condensation between 4-bromobenzonitrile and benzophenone gives 2-(4-bromophenyl)-3,3-diphenylacrylonitrile (Scheme 4). Metathesis of the bromine atom for boronpinacolate proceeds in good yield using the method of Miyaura.39 In this case metathesis of bromine using the n-BuLi/B(OiPr)3 protocol is not compatible with the sensitive cyano functionality. Five equivalents of 2-(4-pinacolatoboron-phenyl)-3,3-diphenylacrylonitrile react smoothly with tetrakis(4-bromophenyl)methane using the optimized Pd(dppf)Cl2 catalyzed coupling conditions to yield tetrakis(4,4′-(3,3-diphenylacrylonitrile)-1,1′-biphenyl)methane, C(DPAB)4 in 82% yield, following purification by flash chromatography. Compound C(DPAB)4 has been fully characterized and the details can be found in the Examples.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A related material was prepared in which the vinylic hydrogen of C(DPVBi)4 is substituted with a cyano group. The stabilized LUMO of the cyano-substituted triphenylethene fragment (2,3,3-triphenylacrylonitrile) is expected to enhance electron injection and transport as is observed for CN-PPV.38 Knovenagle condensation between 4-bromobenzonitrile and benzophenone gives 2-(4-bromophenyl)-3,3-diphenylacrylonitrile (Scheme 4). Metathesis of the bromine atom for boronpinacolate proceeds in good yield using the method of Miyaura.39 In this case metathesis of bromine using the n-BuLi/B(OiPr)3 protocol is not compatible with the sensitive cyano functionality. Five equivalents of 2-(4-pinacolatoboron-phenyl)-3,3-diphenylacrylonitrile react smoothly with tetrakis(4-bromophenyl)methane using the optimized Pd(dppf)Cl2 catalyzed coupling conditions to yield tetrakis(4,4′-(3,3-diphenylacrylonitrile)-1,1′-biphenyl)methane, C(DPAB)4 in 82% yield, following purification by flash chromatography. Compound C(DPAB)4 has been fully characterized and the details can be found in the Examples.