scholarly journals Synthesis and Characterization of Photoluminescence Liquid Crystals Based on Flexible Chain-Bearing Pentafluorinated Bistolanes

Crystals ◽  
2020 ◽  
Vol 10 (7) ◽  
pp. 603
Author(s):  
Shigeyuki Yamada ◽  
Masaya Sato ◽  
Tsutomu Konno

The liquid-crystalline (LC) and photophysical properties of molecules are very sensitive to their electronic and molecular aggregate structures. Herein, to shed light on the structure–property relationships of pentafluorinated bistolane-based photoluminescence (PL) liquid crystals (PLLCs) previously reported by our group, we synthesized pentafluorinated bistolanes with variable flexible chains and evaluated their LC and photophysical properties. The incorporation of an oxygen atom (to afford a 2-methoxyethoxy unit) or an oxygen atom and a methyl group (to afford a 1-methoxyprop-2-oxy unit) into the flexible butoxy chain significantly decreased the temperature of the crystalline-to-LC phase transition, and a chiral nematic phase comprising helical molecular aggregates was observed for the chiral 1-methoxyprop-2-oxy group–bearing bistolane. The synthesized bistolanes exhibited strong blue PL in both solution and crystalline phases; the featuring PL characteristics were maintained in the LC phase (produced by the crystalline-to-LC phase transition) except for a slight PL color change. Thus, it was concluded that the PL behavior of pentafluorinated bistolanes can be modulated by the choice of a suitable flexible chain, and the obtained insights are believed to facilitate the application of PLLCs in thermosensing PL materials.

Crystals ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 195 ◽  
Author(s):  
Shigeyuki Yamada ◽  
Kazuya Miyano ◽  
Tomohiro Agou ◽  
Toshio Kubota ◽  
Tsutomu Konno

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.


Soft Matter ◽  
2021 ◽  
Author(s):  
Vinod Kumar Vishwakarma ◽  
Achalkumar Ammathnadu Sudhakar

Quinoxaline derivatives with different molecular structures stabilizing liquid crystalline self-assembly are discussed in this review. This class of molecules can be systematically modified with careful molecular engineering to achieve different...


2014 ◽  
Vol 43 (13) ◽  
pp. 4778-4823 ◽  
Author(s):  
Hua Lu ◽  
John Mack ◽  
Yongchao Yang ◽  
Zhen Shen

The structure–property relationships of red/NIR region BODIPY dyes is analyzed, so that trends in their photophysical properties can be readily compared.


2019 ◽  
Author(s):  
Richard Mandle ◽  
John W. Goodby

We compare the order parameters, orientational distribution functions (ODF) and heliconical tilt angles of the TB phase exhibited by a liquid-crystalline dimer (CB7CB) to a tetramer (O47) and hexamer (O67) by SAXS/WAXS. Following the N-TB phase transition we find that all order parameters decrease, and while 〈P2 〉 remains positive 〈P4 〉 becomes negative. For all three materials the order parameter 〈P6 〉 is near zero in both phases. The ODF is sugarloaf-like in the nematic phase and volcano-like in the TB phase, allowing us to estimate the heliconical tilt angle of each material and its thermal evolution. The heliconical tilt angle appears to be largely independent of the material studied despite the differing number of mesogenic units.


1989 ◽  
Vol 175 ◽  
Author(s):  
S.H. Chen ◽  
M.L. Tsai ◽  
S.D. Jacobs

AbstractChiral nematic copolymers based on optically active cholesterol, dihydrocholesterol, (R)-(+)- and (S)-(−)-1-phenylethylamine, and (+)- and (−)- isopinocampheol were synthesized and characterized for the investigations of thermotropic and optical properties. Although helical sense does not appear to correlate with the sign of [α]D of the precursor chiral compound as suggested by the observations of cholesteryl and dihydrocholesteryl copolymers, the inversion of chirality in the pendant group, (R)-(+)- vs (S)-(−)-1-phenylethylamine, does lead to the opposite handedness in the resultant helical structure. To better understand the structure-property relationships involving helical sense and twisting power, systematic studies of the roles played by both nematogenic and chiral structures as well as other structural features of the comonomers should be conducted.


2020 ◽  
Vol 16 ◽  
pp. 674-680 ◽  
Author(s):  
Zeguo Fang ◽  
Nawaf Al-Maharik ◽  
Peer Kirsch ◽  
Matthias Bremer ◽  
Alexandra M Z Slawin ◽  
...  

This paper describes the synthesis of a series of organic liquid crystals (LCs) containing selectively fluorinated cyclopropanes at their termini. The syntheses used difluorocarbene additions to olefin precursors, an approach which proved straightforward such that these liquid crystal candidates could be efficiently prepared. Their physical and thermodynamic properties were evaluated and depending on individual structures, they either displayed positive or negative dielectric anisotropy. The study gives some guidance into effective structure–property relationships for the design of LCs containing selectively fluorinated cyclopropane motifs.


Molecules ◽  
2019 ◽  
Vol 25 (1) ◽  
pp. 32 ◽  
Author(s):  
Siyang Ding ◽  
Bicheng Yao ◽  
Louis Schobben ◽  
Yuning Hong

Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure–property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.


Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 997-1002 ◽  
Author(s):  
Carlos Cruz ◽  
Silvia Castro-Fernández ◽  
Ermelinda Maçôas ◽  
Alba Millán ◽  
Araceli Campaña

The controlled preparation of well-defined distorted nanographenes by a bottom-up approach based on organic synthesis permits the direct establishment of unprecedented structure–property relationships in carbon nanostructures. The simultaneous incorporation of various defects in nanographenes affords highly curved structures with novel or enhanced photophysical properties. In this sense, we recently reported a fully helical and saddle-shaped nanographene ribbon containing the first undecabenzo[7]helicene unit. Both its linear and nonlinear optical properties are enhanced in comparison with those of other partially π-extended [7]helicenes. Moreover, the new superhelicene exhibits the highest emission dissymmetry factor (g lum) reported to date for a homochiral nanographene. The combination of both nonlinear and chiroptical properties in nanographenes opens up new possible future applications for those distorted nanostructures.1 Introduction2 Synthesis of Embedded Seven-Membered Rings3 Combination of Defects: Seven-Membered Rings and π-Extended Helicenes4 Conclusions and Outlook


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