Structure and electronics in 1H-pyrrol-2-ylmethylene compounds

Briana R. Schrage; Victor N. Nemykin; Christopher J. Ziegler

doi:10.1016/j.tet.2020.131149

Structure and electronics in 1H-pyrrol-2-ylmethylene compounds

Briana R. Schrage, Victor N. Nemykin, Christopher J. Ziegler

Radiochemical Process Development

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6 Scopus citations

Abstract

In this report, we present the synthesis and characterization of 1H-pyrrol-2-ylmethylenes, prepared from Knoevenagel condensations between pyrrole aldehydes and several organic CH acids. New compounds were characterized by a variety of spectroscopic methods, electrochemistry as well as X-ray crystallography. DFT calculations on these compounds indicates an appreciable amount of electronic delocalization between the pyrrole and acid-derived alkene units. The compounds display a single intense π→π∗ transitions in the UV–visible region. Ab initio and semi-empirical calculations suggest that the HOMO to LUMO single-electron excitations are responsible for the most intense absorption in new chromophores.

Original language	English
Article number	131149
Journal	Tetrahedron
Volume	76
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2020.131149
State	Published - May 8 2020

Funding

Generous support from the Minnesota Supercomputing Institute, NSERC, University of Manitoba, and WestGrid Canada to V.N.N. is greatly appreciated.

Keywords

Chromophores
DFT calculations
Organic acids
Pyrrole
X-ray crystallography

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10.1016/j.tet.2020.131149

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title = "Structure and electronics in 1H-pyrrol-2-ylmethylene compounds",

abstract = "In this report, we present the synthesis and characterization of 1H-pyrrol-2-ylmethylenes, prepared from Knoevenagel condensations between pyrrole aldehydes and several organic CH acids. New compounds were characterized by a variety of spectroscopic methods, electrochemistry as well as X-ray crystallography. DFT calculations on these compounds indicates an appreciable amount of electronic delocalization between the pyrrole and acid-derived alkene units. The compounds display a single intense π→π∗ transitions in the UV–visible region. Ab initio and semi-empirical calculations suggest that the HOMO to LUMO single-electron excitations are responsible for the most intense absorption in new chromophores.",

keywords = "Chromophores, DFT calculations, Organic acids, Pyrrole, X-ray crystallography",

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T1 - Structure and electronics in 1H-pyrrol-2-ylmethylene compounds

AU - Schrage, Briana R.

AU - Nemykin, Victor N.

AU - Ziegler, Christopher J.

PY - 2020/5/8

Y1 - 2020/5/8

N2 - In this report, we present the synthesis and characterization of 1H-pyrrol-2-ylmethylenes, prepared from Knoevenagel condensations between pyrrole aldehydes and several organic CH acids. New compounds were characterized by a variety of spectroscopic methods, electrochemistry as well as X-ray crystallography. DFT calculations on these compounds indicates an appreciable amount of electronic delocalization between the pyrrole and acid-derived alkene units. The compounds display a single intense π→π∗ transitions in the UV–visible region. Ab initio and semi-empirical calculations suggest that the HOMO to LUMO single-electron excitations are responsible for the most intense absorption in new chromophores.

AB - In this report, we present the synthesis and characterization of 1H-pyrrol-2-ylmethylenes, prepared from Knoevenagel condensations between pyrrole aldehydes and several organic CH acids. New compounds were characterized by a variety of spectroscopic methods, electrochemistry as well as X-ray crystallography. DFT calculations on these compounds indicates an appreciable amount of electronic delocalization between the pyrrole and acid-derived alkene units. The compounds display a single intense π→π∗ transitions in the UV–visible region. Ab initio and semi-empirical calculations suggest that the HOMO to LUMO single-electron excitations are responsible for the most intense absorption in new chromophores.

KW - Chromophores

KW - DFT calculations

KW - Organic acids

KW - Pyrrole

KW - X-ray crystallography

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JO - Tetrahedron

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Structure and electronics in 1H-pyrrol-2-ylmethylene compounds

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