Synthesis and Two‐Photon Absorption Properties of Symmetrical Chromophores Derived from 2,3,5‐Trisubstituted Quinoxaline Units

Abstract

A set of symmetrically substituted multibranched chromophores composed of three quinoxaline‐based congeners has been synthesized and experimentally shown to possess strong and widely dispersed two‐photon absorptivities in the visible to near‐IR region under the irradiation of femtosecond and nanosecond laser pulses. The electronic properties of the central π bridges incorporated into the final structures are closely connected to the molecular two‐photon activities of these model compounds. Effective optical‐power attenuation and stabilization behaviors in the nanosecond time domain of these dye molecules were also investigated. The structural motif of these compounds provides a useful approach for the molecular design of strong two‐photon absorbing material systems with the potential for quick‐responsive and broadband optical‐control related applications, particularly for long‐duration laser pulses in the near‐IR region.

Nonlinear Optical Materials for the Smart Filtering of Optical Radiation

“…Several multibranched chromophores containing 2,3-diarylquinoxalinyl units ( 329 – 338 , Charts and ) as the electron acceptors have been synthesized for the measurement of their NLO properties. − Most of these compounds possess strong and broad TPA in the NIR region, reaching effective optical-power-attenuation both in fs and in ns time domains. Expansion of the size of the π-conjugated system, through the insertion of different aromatic rings, gave a positive contribution for the enhancement of TPA.…”

“…Expansion of the size of the π-conjugated system, through the insertion of different aromatic rings, gave a positive contribution for the enhancement of TPA. The insertion of the electron-rich dialkoxybenzene unit provided a larger increment of molecular TPA, 889,890 exhibiting both intense upconverted emission when excited by two-photon process and effective OPL/stabilization properties upon excitation with ns laser pulses. 889,890 Compound 339 (Chart 65) was also studied for NLO, under excitation at 800 nm with 8 ns laser pulses at the repetition rate of 10 Hz.…”

From Light to Structure: Photo Initiators for Radical Two‐Photon Polymerization

“…Besides the mentioned heterocycles, quinoxaline compounds were investigated as sensitizers for solar cells components and as two‐photon absorption dyes [106–108] . Cao et al.…”

“…Besides the mentioned heterocycles, quinoxaline compounds were investigated as sensitizers for solar cells components and as two-photon absorption dyes. [106][107][108] Cao et al investigated compounds consisting of a quinoxaline and benzoquinoxaline as acceptor combined with modified triphenylamine and ethoxybenzene as donor groups (Figure 48). [109] The four initiators show absorption maxima between 350 and 470 nm (Table 17).…”

α‐Nitro Epoxides in Organic Synthesis: Development of a One‐Pot Organocatalytic Strategy for the Synthesis of Quinoxalines

“…Among such macromolecular compounds of natural origin, the preparation of low‐weight molecules comprising the quinoxaline moiety leads to compounds with promising bioactivity against hepatitis C, depression,2 and cancer (Figure 1). 3,4 Owing to its extended π‐system, the quinoxaline heterocycle is also incorporated in macromolecular dyes for dye‐sensitized solar cells (DSSCs)5,6 and photoabsorbent7 or electroluminescent materials 8…”