Isolation and characterization of conformational isomers of N, N′‐bis(3, 5‐dichlorosalicylidene)‐2, 2′‐ethylenedianiline: crystal structure, photoluminescence, and density functional theory calculation. (9th October 2014)

• Record Type: Journal Article
• Authors: Min, Kil Sik; Kim, Yoon Jae; Ko, Hyun Jin; Kwak, Dae Hyun; Kim, Tae Wook; Shin, Jong Won; Kim, Bong Gon
• Is Part Of: Journal of physical organic chemistry. Volume 27:Number 12(2014:Dec.)
• Page Start: 960
• Page End: 966
• Publication Date: 2014-10-09
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3379
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>We have isolated two isomeric solids <bold>1</bold> and <bold>2</bold> of <italic>N</italic>, <italic>N</italic>′‐bis(3, 5‐dichlorosalicylidene)‐2, 2′‐ethylenedianiline and characterized by IR, UV/Vis, X‐ray <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">powder diffraction</named-content>, thermogravimetric analysis/differential thermal analysis, and X‐ray crystallography. Although the solids are same formulas, each shows different colors and crystal structures. Orange solid (<bold>1</bold>) shows endo conformation while yellow solid (<bold>2</bold>) exhibits exo form depending on packing modes. UV/Vis spectra of <bold>1</bold> and <bold>2</bold> appear very similar patterns in the solid state; however, the bands of <bold>1</bold> are slightly red‐shifted compared with those of <bold>2</bold>. <bold>1</bold> displays a strong fluorescent emission band at ~582 nm while <bold>2</bold> shows an intense fluorescent signal at ~563 nm. The charge density populations of <bold>1</bold> and <bold>2</bold> have been studied by computational simulations using density functional theory at pbe1pbe/6‐311G** level. The calculated highest occupied molecular orbital and lowest unoccupied molecular orbital energies of <bold>1</bold> and <bold>2</bold> confirm that <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">charge transfer</named-content> occurs within the organic molecules. The energy difference of HOMO‐LUMO in <bold>1</bold> is smaller slightly than that of <bold>2</bold> about 0.05 eV (~17 nm). Copyright © 2014 John Wiley & Sons, Ltd.</p> </abstract>