Synthesis and TDDFT Investigation of New Maleimide Derivatives Bearing Pyrrole and Indole Ring

Yasuhiro Shigemitsu,Naoko Mizuyama,Masayori Hagimori,Yoshinori Tominaga,Kaori Komiya

doi:10.1155/2009/413219

Abstract

A novel series of heterocycles were obtained through the condensation reaction of 4-methylthiomaleimides with pyrroles and indoles. The newly synthesized compounds exhibit their major electronic absorption peaks ranging 435–504 nm in solution at room temperature. Time-dependent density-functional theory (TDDFT) calculations were systematically performed in order to elucidate their structure-color relationships, using a set of exchange-correlation (XC) functionals. The TDDFT computational scheme employing PCM-TDDFT/6-31+G(d,p)//DFT/6-311G(d,p) level of theory gave qualitatively satisfactory results in their predictions.

Highlights

Maleimides are widely known as active electrophilic reagents to readily react with a variety of dienes and 1,3-dipoles including azomethine ylide, carbonyl ylide and, nitorenes, leading to various heterocycles [1]
We have explored the abundant synthetic potential of the new functionalized maleimides which can effectively be converted to fused pyridazine derivatives [2] and polymethine dyes [3, 4]
The computational investigations are described for their first intense electric absorption peaks using TD-DFT [5], which is widely used in electronic transition energy predictions for many molecules [6, 7]

Summary

Introduction

Maleimides are widely known as active electrophilic reagents to readily react with a variety of dienes and 1,3-dipoles including azomethine ylide, carbonyl ylide and, nitorenes, leading to various heterocycles [1]. We have explored the abundant synthetic potential of the new functionalized maleimides which can effectively be converted to fused pyridazine derivatives [2] and polymethine dyes [3, 4]. We report the new series of dyes bearing push (pyrrole, indole)— pull (maleimide) systems. The computational investigations are described for their first intense electric absorption peaks using TD-DFT [5], which is widely used in electronic transition energy predictions for many molecules [6, 7]

Synthesis and Electronic Spectra

Computational Details

Results and Discussion

Conclusion