Synthesis and multi-photon absorption properties of symmetric bisarylacetylene chromophores using functionalized isomeric pyrazinoindenocarbazole units as the rigid aryl substituents

Tzu Chau Lin, Jhe Yi Lin, Bo Kai Tsai, Nai Yi Liang, Wei Chien

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A pair of isomeric chromophores based on the skeleton of bisarylacetylene using functionalized pyrazinoindenocarbazole moieties as the aryl substituents has been synthesized and characterized for their two- and three-photon-related properties in the femtosecond and nanosecond regimes. Our experiments have found that both model fluorophores manifest strong two-photon absorption in the near infrared region with one of the isomers exhibiting superior maximum two-photon absorptivity. It is realized that both the isomeric forms of functionalized pyrazinoindenocarbazoles are useful π-units for the construction of highly two-photon active materials but the effectiveness of the units is unequal, which is probably attributed to the difference of their conjugated structures. Two-photon-based optical power-limiting and stabilization against nanosecond laser pulses of one isomer was demonstrated. Additionally, these two chromophores exhibit strong three-photon-induced fluorescence when excited by the nanosecond laser with longer wavelengths (≥1000 nm), implying their potential utility to serve as prototypes for the development of three-photon materials.

Original languageEnglish
Pages (from-to)347-359
Number of pages13
JournalDyes and Pigments
Volume132
DOIs
StatePublished - 1 Sep 2016

Keywords

  • Optical power-limiting
  • Pyrazinoindenocarbazole
  • Sonogashira reaction
  • Three-photon absorption
  • Two-photon absorption

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