N-fused ring strategy toward orange/yellow light-emitting liquid crystalline molecules

Liu, Tingting; Zhu, Dezhao; Zhang, Mei; Cui, Ming; Li, Qingfang; Fan, Yun; Wang, Hui; Zhang, Zhuo

doi:10.1016/j.dyepig.2018.06.016

Cited by 11 publications

(4 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[39] Further, fluorazone, a derivative of pyrrolo [1,2-a]indole has been used as a dye sensitizers for photovoltaics and dye-sensitized solar cell (DSSC) applications. [40,41] Depending upon conjugation and place of sp 3 carbon, pyrrolo [1,2-a]indole scaffold has three structural isomers namely, 9Hpyrrolo [1,2-a]indole V, 1H-pyrrolo [1,2-a]indole VI and 3H-pyrrolo [1,2-a]indole VII. [28] Owing to their diverse applications, many synthetic protocols for the synthesis of pyrrolo [1,2-a]indoles have been developed.…”

Section: Introductionmentioning

confidence: 99%

“…Pyrrolo[1,2‐ a ]indoles have been used as anticancer, [31,32] antiparasitic, [34] antimalarial, [33] anti‐HIV, [35] and central nervous system (CNS) stimulating agents [39] . Further, fluorazone, a derivative of pyrrolo[1,2‐ a ]indole has been used as a dye sensitizers for photovoltaics and dye‐sensitized solar cell (DSSC) applications [40,41] . Depending upon conjugation and place of sp 3 carbon, pyrrolo[1,2‐ a ]indole scaffold has three structural isomers namely, 9 H ‐pyrrolo[1,2‐ a ]indole V , 1 H ‐pyrrolo[1,2‐ a ]indole VI and 3 H ‐pyrrolo[1,2‐ a ]indole VII [28] .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of 3H‐Pyrrolo‐(1,2‐a) Indole‐based Fluorophore Macrocycles and their Stable Cation Radicals

2021

View full text Add to dashboard Cite

Small molecular fluorophores with high quantum yields are of particular interest because of their role in several applications that range from ion sensing to bioimaging. Indole based biomolecules are well known for their fluorescence properties. Pyrrolo[1,2-a]indoles have gained tremendous interest in recent times due to their applicability in various fields such as biomedicine and dye-sensitized solar cells (DSSC). In this article, we report the synthesis of new types of crowned 3H-pyrrolo[1,2-a]indole fluorophore macrocycles 1-3 which were prepared in 30-35% yields using commercially available compounds under simple reaction conditions. These fluorophore macrocycles 1-3 were charac-terized by HR-MS, 1D & 2D NMR, X-ray crystallography, absorption, fluorescence, electrochemical, and DFT/TD-DFT studies. The fluorophores 1-3 absorb in the region of 465-480 nm and emit in the region of 615-645 nm with large Stokes shift (~150 nm), 10-20% quantum yields, and singlet state lifetimes of 1.70-2.50 ns. The electrochemical studies revealed that macrocycles 1-3 are electron-rich and undergo easier oxidations. The macrocycles 1-3 readily form cation radicals by chemical and electrochemical oxidation which are highly stable at low temperatures as well as at room temperature.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 3H‐Pyrrolo‐(1,2‐a) Indole‐based Fluorophore Macrocycles and their Stable Cation Radicals

2021

View full text Add to dashboard Cite

show abstract

“…Recently, our group developed families of pentafluorinated tolane [13] and bistolane derivatives with alkoxy-type flexible chains (Figure 1a) [14,15] as promising LE materials and revealed that their PL can change depending on the electron-density distribution [16] or the molecular arrangement in the aggregated structure [13][14][15]. It was of great interest that the bistolane-type LE molecules showed not only PL, but also liquid-crystalline (LC) properties, namely light-emitting liquid crystals 2 of 16 (LELCs) [17][18][19][20], and the PL behaviors were found to change through the crystal (Cr) LC thermal phase transition. In addition, we recently developed novel LELCs with V-or Y-shaped molecular geometry, which showed intriguing switching characteristics induced by thermal stimulus [21].…”

Section: Introductionmentioning

confidence: 99%

2-Chloroalkoxy-Substituted Pentafluorinated Bistolanes as Novel Light-Emitting Liquid Crystals

et al. 2019

View full text Add to dashboard Cite

In this study, we designed and synthesized novel pentafluorinated bistolane derivatives with 2-chloropentyl or 2-chlorohexyl flexible units as novel light-emitting liquid crystals (LELCs). By measuring the phase-transition behaviors, all derivatives were found to display liquid-crystalline (LC) phases during both heating and cooling processes. Among the novel bistolanes, the S- and R-configured derivatives exhibited a chiral nematic (N*) phase with a typical Grandjean optical texture. Interestingly, the chiral derivatives also exhibited a blue phase with a typical platelet texture in a narrow temperature range (2–4 °C). Photophysical measurements revealed that the 2-chloroalkoxy-substituted pentafluorinated bistolanes exhibited intense photoluminescence (PL) both in solution and in crystalline phases. The PL characteristics, especially the maximum PL wavelength, were found to switch sensitively during the heating and cooling cycles depending on the molecular aggregates through the crystal (Cr) ⇄ N* phase transition. The 2-chloroalkoxy flexible units induced dynamic changes in the LC and PL properties, providing valuable insight into the potential of various LELCs as PL sensing materials.

show abstract

“…Photovoltaic devices displayed moderate power conversion efficiencies of 2.1–2.4 %. Zeng et al synthesized light‐emitting liquid crystalline compounds 191 – 192 . These fluorinated and non‐fluorinated 7‐(arylethynyl)‐9 H ‐pyrrolo[1,2‐ a ]indol‐9‐ones displayed yellow (for 191 ) and orange (for 192 ) fluorescence.…”

Section: Applicationsmentioning

confidence: 99%

Synthesis and Applications of 9H‐Pyrrolo[1,2‐a]indole and 9H‐Pyrrolo[1,2‐a]indol‐9‐one Derivatives

Lorton

Voituriez

2019

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

N-fused ring strategy toward orange/yellow light-emitting liquid crystalline molecules

Cited by 11 publications

References 28 publications

Synthesis of 3H‐Pyrrolo‐(1,2‐a) Indole‐based Fluorophore Macrocycles and their Stable Cation Radicals

Synthesis of 3H‐Pyrrolo‐(1,2‐a) Indole‐based Fluorophore Macrocycles and their Stable Cation Radicals

2-Chloroalkoxy-Substituted Pentafluorinated Bistolanes as Novel Light-Emitting Liquid Crystals

Synthesis and Applications of 9H‐Pyrrolo[1,2‐a]indole and 9H‐Pyrrolo[1,2‐a]indol‐9‐one Derivatives

Contact Info

Product

Resources

About