Trans-cis isomerization assisted synthesis of solution-processable yellow fluorescent maleic anhydrides for white-light generation

Ozdemir M., GENÇ S., ÖZDEMİR R., ALTINTAS Y., Citir M., Sen U., ...More

SYNTHETIC METALS, vol.210, pp.192-200, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 210
  • Publication Date: 2015
  • Doi Number: 10.1016/j.synthmet.2015.09.027
  • Journal Name: SYNTHETIC METALS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.192-200
  • Keywords: Maleic anhydride, Trans-to-cis isomerization synthesis, White light emitting diode (WLED), Wavelength-upconverting material, BIOLOGICAL EVALUATION, THIOPHENE COPOLYMERS, EMITTING-DIODES, SEMICONDUCTORS, DERIVATIVES
  • Eskisehir Osmangazi University Affiliated: No


Heterocyclic maleic anhydride derivatives have been extensively studied in natural products chemistry over the past few decades. However, their incorporation into optoelectronic devices has lagged behind that of other pi-conjugated systems, and they have never been studied in white light emitting diodes (WLEDs). The development of emissive pi-conjugated materials for (WLEDs) has been an emerging scientific and technological research area to replace phosphors used in LED-based solid-state lighting. Here, we demonstrate the design, synthesis and characterization of two new highly emissive alkyl-substituted bis(thienyl)maleic anhydrides (C6-Th2MA and C12-Th2MA) with favorable photophysical properties. The new core is synthesized via a novel trans-to-cis isomerization-assisted one-pot reaction, which is demonstrated for the first time in the literature for the synthesis of a bis(heteroaryl)maleic anhydride. Due to its favorable absorption and fluorescence properties in the blue and yellow region of the visible spectrum, respectively, C12-Th2MA is studied as a potential wavelength-upconverting material. A WLED fabricated by drop-casting a polymeric solution of C12-Th2MA on a blue LED (InGaN, 455 nm) yields promising CIE coordinates and color-rendering index (CRI) values of (0.24, 0.20) and 65.0, respectively. Considering the simplicity of the current molecular structure and facile synthesis, alkyl-substituted bis(thienyl)maleic anhydrides stand as ideal phosphor alternatives. Therefore, the current findings may open new perspectives for the development of maleic anhydride-based small molecules for low-cost, energy-efficient, and solution-processed lighting technologies. (C) 2015 Elsevier B.V. All rights reserved.