Synthesis and non-linear optical properties of mono-pyrrolotetrathiafulvalene derived donor–π–acceptor dyads

Abstract

The synthesis of novel donor-p-acceptor dyads based on a pyrrolo-annelated tetrathiafulvalene unit is described. The linear and non-linear optical properties of these chromophores have been investigated, together with their redox properties. For a dyad containing a p-nitrophenyl acceptor group, a significant third-order optical non-linearity is observed.

An Experimental and Computational Study on Intramolecular Charge Transfer: A Tetrathiafulvalene‐Fused Dipyridophenazine Molecule

“…Unless stated otherwise, all other reagents were purchased from commercial sources and used without additional purification. 1,2-Diamino-benzene-4,5-bis(thiocyanate), [28] 4,5-bis(propylthio)-1,3-dithiole-2-one, [29] and 1,10-phenanthroline-5,6-dione [30] were prepared according to literature procedures. Elemental analyses were performed on an EA 1110 Elemental Analyzer CHN Carlo Erba Instruments.…”

Ethyl 2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiolo[4,5-c]pyrrole-4-carboxylate

“…For background to tetrathiafulvalenes, see: Jeppesen et al (1999); Hansel et al (2004). For details of the synthesis, see: .…”

“…Recently, Hansel reported a series of novel donor-π-acceptor dyads with pyrrolo-annelated tetrathiafulvalene units, which possess significant third-order nonlinear optical properties (Hansel et al, 2004). In this paper, we describe the crystal structure of the title compound (I), which is a key precursor of the dyads.…”

2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde

“…For background to tetrathiafulvalenes, see: Jeppesen et al (1999); Hansel et al (2004). For the synthesis, see: An et al (2009).…”