Fluorescent thiophene-based materials and their outlook for emissive applications

Rasmussen, Seth C.; Evenson, Sean J.; McCausland, Casey B.

doi:10.1039/c4cc09206f

Cited by 175 publications

(108 citation statements)

References 157 publications

Supporting

Mentioning

101

Contrasting

Order By: Relevance

“…As reported by Rasmussen and coworkers, oligothiophene materials have high quantum yields as well as significant solid-state emission. 23,24 End-capping DTP oligomers with thienyl groups produced red-shifted absorption and emission maxima in comparison to phenyl end-caps. 23 Yam et al .…”

Section: Introductionmentioning

confidence: 99%

Stimuli responsive furan and thiophene substituted difluoroboron β-diketonate materials

Morris

Butler

Kołpaczyńska

et al. 2017

Mater. Chem. Front.

View full text Add to dashboard Cite

Difluoroboron β-diketonate (BF2bdk) compounds exhibit solid-state switchable luminescence under excitation by UV light. This property is usually manifested as a blue-shift in emission when dye films are thermally annealed followed by a red-shift in response to mechanical shear (i.e. mechanochromic luminescence). Here we report thiophene and furan heterocycle-substituted dyes bearing short methoxy and long dodecyloxy chain substituents. Optical properties of the dyes were investigated in solution, pristine powders, and films on paper and glass. The structural and thermal properties of the dyes were also investigated by powder x-ray diffraction (XRD) and differential scanning calorimetry (DSC), respectively. The methoxy-substituted dyes exhibited neither thermal nor mechano-responsive behavior, however, addition of a longer C12 alkoxyl chain substituent resulted in stimuli-responsive behavior. The furan and thiophene dodecyloxy-substituted dyes both exhibit high-contrast reversible luminescence switching between crystalline, blue-shifted and amorphous red-shifted emissive states. For the furan dye, gentle heating produced a green emissive form while melting followed by rapid cooling produced an orange emissive form. The thiophene dye, on the other hand, exhibited blue-shifted emission when annealed below its melting temperature and red-shifted emission when smeared with a cotton swab (mechanochromic luminescence). These transformations for both dyes were found to be completely reversible, making them potential candidates for applications requiring reusable, functional materials.

show abstract

Section: Introductionmentioning

confidence: 99%

Stimuli responsive furan and thiophene substituted difluoroboron β-diketonate materials

Morris

Butler

Kołpaczyńska

et al. 2017

Mater. Chem. Front.

View full text Add to dashboard Cite

show abstract

“…Since then, conjugated materials have received ever increasing interest resulting from the fact that these systems combine the electronic and optical properties of classical inorganic semiconductors with many of the desirable properties of organic plastics [12,13]. This eventually resulted in the current field of organic electronics, with efforts focused on the development of technological applications such as sensors, electrochromic devices, organic photovoltaics (OPVs), organic light-emitting diodes (OLEDs), and field effect transistors (FETs) [12,13,14,15,16,17,18,19]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Electropolymerization of Extended Fused-Ring Thieno[3,4-b]pyrazine-Based Terthienyls

2016

View full text Add to dashboard Cite

The synthesis, characterization, and electropolymerization of a series of extended fused-ring thieno[3,4-b]pyrazine-based terthienyls are reported. The target terthienyls contain a central extended thieno[3,4-b]pyrazine analogue containing 2-thienyl units at the reactive α-positions of the central thiophene. The extended fused-ring thieno[3,4-b]pyrazine analogues studied include acenaphtho[1,2-b]thieno[3,4-e]pyrazine, dibenzo[f,h]thieno[3,4-b]quinoxaline, and thieno[3′,4′:5,6]-pyrazino[2,3-f][1,10]phenanthroline. Comparison of the electrochemical and photophysical properties to simple thieno[3,4-b]pyrazine-based terthienyls and their polymeric analogues are reported in order to provide structure-function relationships within this series of compounds and materials.

show abstract

“…This short review aims to give a concise summary of polymers with side-chain thiophene-based functionalities, which can be prepared either by controlled polymerization techniques (e.g., ATRP, ROMP, and RAFT) or postpolymerization modification, and to introduce their properties and applications based on some recent or well-representative examples, which includes flexible polymer precursors to conjugated polymers, light-emitting polymeric materials as active components in electroluminescent devices, light-absorbing polymeric materials as active layers in photovoltaic cells, self-assembling amphiphilic block copolymers as functional nanomaterials, surface modification for novel hybrid nanocomposites, etc. Numerous reviews on main-chain thiophene-containing polymers can be found elsewhere [9,11,15,27,28]. This review will be limited to non-conjugated polymers with thiophene-based oligomers as pendant groups.…”

Section: Introductionmentioning

confidence: 98%

Progress in side-chain thiophene-containing polymers: synthesis, properties and applications

2015

View full text Add to dashboard Cite

In contrast to conventional main-chain conjugated polymers, incorporation of electronically active conjugated oligomers into non-conjugated polymer backbones as pendant groups represents a promising alternative strategy to developing novel electroactive polymer materials that are desirable for potential applications in organic electronics. This review focuses on polymers with thiophene in the side chain and summarizes the most important synthetic approaches to these polymers, including direct controlled polymerization techniques (e.g., ATRP, ROMP, and RAFT) as well as post-polymerization modifications. Additionally, various properties and applications of these polymers are discussed.

show abstract

Fluorescent thiophene-based materials and their outlook for emissive applications

Cited by 175 publications

References 157 publications

Stimuli responsive furan and thiophene substituted difluoroboron β-diketonate materials

Stimuli responsive furan and thiophene substituted difluoroboron β-diketonate materials

Synthesis, Characterization, and Electropolymerization of Extended Fused-Ring Thieno[3,4-b]pyrazine-Based Terthienyls

Progress in side-chain thiophene-containing polymers: synthesis, properties and applications

Contact Info

Product

Resources

About