Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Abstract

-Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.

Molybdenum Complexes Bearing (Bi)thienyl‐ or Arylthienyl‐Substituted π‐Conjugated Spacers: Synthesis, Electrochemical, Spectroscopic and Nonlinear Optical Properties

“…[45] The arylthienyl moiety will act not only as a spacer but also as an auxiliary donor. These findings are in accordance with our recent work [19,[46][47][48] in which we concluded that the increase or decrease of the molecular nonlinear activity of heteroaromatic systems depends not only on the electronic nature of the (hetero)aromatic rings but also on the position of substitution of the donor or acceptor groups on these systems.…”

Highly efficient and thermally stable NLO organic materials based on pyrrole and thiophene heterocycles

“…spectra is observed when stronger acceptor groups are linked to the heterocyclic system. [8][9][10][11][12][19][20] As a result the substitution of a formyl group for a 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile moiety leads to a red shift of 170 nm from 348 nm (1a) to 510 nm (1e). Within the series 1a-e the CT bands moves to lower energy as the electron accepting ability of the acceptor moiety increases, in the order CHO < dicyanovinyl < rhodanine < thiobarbituric acid < 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (Fig.…”

“…Recently we were able to overcome these difficulties and reported on the interesting electrochemical and solvatochromic properties and the first hyperpolarizabilities of pyrrolecontaining NLO chromophores with potential application as nonlinear optical compounds. [8][9][10][11][12] We were therefore motivated to extend these studies and explore the potential of a novel series 1-(4-(thiophen-2-yl)phenyl)-1H-pyrroles 1 as efficient push-pull systems bearing pyrrole as donor group and dicyanovinyl, rhodanine, thiobarbituric acid and indanonedicyanovinyl as acceptor moieties linked through an arylthiophene spacer.…”

Linear and non-linear optical properties of 2,5-disubstituted pyrroles supported by a catalyst-free SiO2 sonogel network

“…Experimental [28], and theoretical [29][30][31] studies have demonstrated that replacing the benzene ring of a chromophore bridge with easily delocalizable five membered heteroaromatic rings as a pyrrole, results in an enhanced molecular polarizability of donor-acceptor compounds, where the pyrrole ring acts as electron-withdrawing structure [32]. Due to their solvatochromic, electrochemical and nonlinear optical properties, donor-acceptor pyrrole derivates could be employed for the manufacture of semiconductor materials or materials with strong NLO-responses [32,33]. Furthermore, pyrrole and oligomers synthesis has increased due to their application as electroluminescent devices [34].…”