NMR studies of the reaction between amino-phenylene vinylene thiophene and tetracyanoethylene

✍ Scribed by Jianfu Ding; Gilles P. Robertson; Jianping Lu

• Book ID: 104095306
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 335 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.04.020

✦ Synopsis

Amino tricyanovinyl thiophene chromophores (A-TCVT) are prepared by a substitution reaction of amino-phenylene vinylene thiophene (A-PVT) with tetracyanoethylene (TCNE). This reaction does not occur directly. The vinylene double bond in the PVT unit first reacts rapidly with TCNE to form a [2+2] cycloaddition product. It is then reverted to PVT unit prior to the subsequent substitution at 50 °C. This reversible cycloaddition converts the cis-isomer of PVT units into the trans-counterparts, thus the final TCNE substituted products can be expected for a better performance as non-linear optical materials.