Current Research in Bioorganic & Organic Chemistry (ISSN: 2639-4685)

research article

Effect of Remote Polyene Bridge Methyl Substituent onPhysical Properties of Dipolar Chromophores with Conformationally and Configurationally Locked Polyene Bridge

Godson C.Nwokogu*, Samuel Simpson

Department of Chemistry and Biochemistry, Hampton University, Hampton, VA 23668, USA

*Corresponding author:Godson C. Nwokogu, Department of Chemistry and Biochemistry, Hampton University, Hampton, VA 23668, USA.  Tel: +17577275276; Email:godson.nwokogu@hamptonu.edu

Received Date: 28 January, 2019; Accepted Date:11February, 2019; Published Date:19 February, 2019

Abstract

The effect of a C-2 substituent on the success of Knoevenagel condensation of the cycloalkenone moiety,which is usually the final stepinthe multi-step synthesis of conformationally and configurationally locked polyene bridged Donor -p- Acceptor chromophores, has been investigated.  In addition, the possibility of a two-pot synthesis of polyene bridges with more than two annulated cyclohexenylrings and the effect of a polyene bridge methyl substituent on the planarity of the chromophore have been investigated. The results of these studies show that a C-2 on the terminal cycloalkenone of the polyenone must not be substituted for successful Knoevenagel condensation in the modular synthesis of Donor-p-Acceptor dipolar chromophores.  It is also demonstrated that three new rings can be annulated in a two-pot reaction sequence.  A significant blue shift in lmax of prepared rigid polyene bridge chromophores indicates that a remote methyl substituent on the polyene bridge has a dramatic effect on the planarity of the chromophore.

Keywords

Blue Shift; Chromophore; Donor-p-Acceptor; Knoevenagel Condensation; Poly-Michael Addition; Polyene Bridge; Poly-Aldol; Remote Methyl Substituent.


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