Synthesis of Chromophores with Extremely High Electro-optic Activity. 1. Thiophene-Bridge-Based Chromophores

Abstract

We have successfully synthesized several new substituted thiophene-based electro-optic chromophores. All of these chromophores have structures similar to FTC but they incorporated our newly designed tricyanovinyldihydrofuran acceptors. Since these acceptors possess an anisotropic structure, all of the chromophores are very soluble in a wide range of organic solvents. Thermal study of these chromophores by TGA shows all of them are very stable in air. UV spectra indicate the chromophores have a large solvatochromic effect, implying very large molecular nonlinearities.

Novel Thiophene‐Thiazolothiazole Copolymers for Organic Field‐Effect Transistors

“…Materials: 3-Dodecylthiophene-2-carbaldehyde (1) [14] and 4,4'-didodecyl-2,2'-bithiophene (5) [15] were prepared according to the literature procedure. N-Bromosuccinimide (NBS) was purchased from Aldrich and recrystallized from water prior to use.…”

Theoretical Investigation on the One‐ and Two‐photon Absorption Properties of Porphyrin‐thiophene Chromophores

“…24 The chromophores were synthesized by Zhang et al 25 In this paper, we theoretically study equilibrium geometries, electronic structures, OPA and TPA properties of conjugated porphyrin-thiophene chromophores.…”

Heterocyclic Nonlinear Optical Chromophores Composed of Phenothiazine or Carbazole Donor and 2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran Acceptor

“…Particularly, 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) was well adopted as a strong electron acceptor that induces significantly high dipole moment (µ), first-order molecular hyperpolarizability (β), and their product (µβ). [8][9][10][11][12][13] In this report, we describe the synthesis and the microscopic nonlinear optical properties of two different types of the heterocyclic chromophores. Additional donor of diethylaminostyryl group was tethered to phenothaizine or carbazole that plays as conjugative donor bridge in DEA-PTZ-TCF and DEA-CBZ-TCF (see Figure 1).…”

“…2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) was commonly employed as a strong electron acceptor to induce strong charge transfer complex. [8][9][10][11][12][13] Energy state diagram to describe the highest occupied molecular orbital (HOMO) energy, the lowest unoccupied molecular orbital (LUMO) energy, and the bandgap were determined by electrochemical analysis and absorption spectroscopic method. The molecular 1 st -order hyperpolarizabilities and the dipole moments of the chromophores were calculated using semiempirical method.…”