A Straightforward Modular Approach to NLO-Activeβ-Amino Vinyl Nitrothiophenes

Abstract

Secondary amines add very efficiently to 2-ethynyl-5-nitrothiophene to give beta-amino vinyl nitrothiophenes, a novel class of push-pull chromophores. According to first HRS measurements these highly solvochromic compounds with relatively short dipole axes display remarkably high static first hyperpolarizabilities = 29-31 x 10(-)(30) esu.

Heteroaromatic Cation‐Based Chromophores: Synthesis and Nonlinear Optical Properties of Alkynylazinium Salts

“…[1] In these systems, particular effort has been made to find the optimum combination of the bridge, acceptor and donor groups with the aim of enhancing the NLO response, particularly with molecules that can be chemically fine-tuned for desired applications. [2] In this context, organic chromophores containing different acceptor units, such as nitro, [3] nitrile, [4] sulfonyl, [5] polycyanovinyl [6] and phosphonate [7] salts, inter alia, have been explored previously. The use of charged moieties as acceptor units is restricted to diazonium salts [8] and some heteroaromatic cations; for example, benzothiazolium [9] and pyridinium salts [10] have been studied as cationic and dicationic acceptors in a few push-pull systems such as those shown in Figure 1.…”

Synthesis and structural characterization of ruthenium(II) and iron(II) complexes containing 1,2-di-(2-thienyl)-ethene derived ligands as chromophores

“…Thiophene moiety has been studied as chromophore both in organic [16][17][18] and organometallic [19][20][21][22][23][24][25] materials for NLO and it is nowadays recognized to exhibit enhanced second-order polarizabilities compared to p-systems with phenylene bridges, mainly due to its lower delocalization energy, leading to a more effective conjugation. We recently reported the synthesis and NLO properties of g 5 -monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile derived ligands [26].…”

Unusual Solid-State Luminescent Push−Pull Indolones: A General One-Pot Three-component Approach

“…As early as 2000, we had developed a multicomponent method for the synthesis of chromophores and fluorophores . This was recently further extended by a domino insertion−coupling sequence of alkynoyl o -iodo anilides 1 , or phenolates 2 , with p -anisyl acetylene ( 3a ) or propargyl allyl ethers 5 , to give an enyne indolone 4 or highly fluorescent structurally rigidified butadienes 6 in a spirocyclic framework in good to excellent yields, displaying extraordinary large Stokes shifts and fluorescence quantum yields Φ f as high as 62% (Scheme ) .…”