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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 22
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Original Articles

Synthesis and photophysical properties of benzo[c]thiophene, p-phenylene-, triphenylamine-, and pyrene-based vinylenes

Meganathan NandakumarDepartment of Organic Chemistry, School of Chemistry, University of Madras, Guindy Campus, Chennai, Tamil Nadu, India
,
Elumalai SankarDepartment of Organic Chemistry, School of Chemistry, University of Madras, Guindy Campus, Chennai, Tamil Nadu, India
&
Arasambattu K. MohanakrishnanDepartment of Organic Chemistry, School of Chemistry, University of Madras, Guindy Campus, Chennai, Tamil Nadu, IndiaCorrespondence[email protected]; [email protected]
Pages 1810-1819 | Received 14 Jul 2016, Published online: 24 Oct 2016
 
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ABSTRACT

An efficient synthesis of benzo[c]thiophenyl/p-phenylenyl/pyrenyl phosphonate esters has been achieved using ZnBr2-catalyzed Michaelis–Arbuzov reaction of corresponding benzyl alcohol/bromides at room temperature. Horner–Wadsworth–Emmons reaction of the phosphonate esters with aryl/heteroaryl aldehydes in the presence of t-BuOK furnished the vinylenes in good yields. The absorption and emission characteristics of the synthesized vinylenes were also reported.

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