Push-pull biphenyl and tolane derivatives as novel luminescent liquid crystals: synthesis and properties

被引:7
作者
Iida, Yuuto [1 ]
Shimomura, Yoshimichi [1 ]
Tokita, Masatoshi [1 ]
Konishi, Gen-ichi [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo, Japan
关键词
Luminescent liquid crystal; push-pull; biphenyl; tolane; nematic phase; 7fluorescence; EXCIMER FORMATION; BIREFRINGENCE; ACCEPTOR; FLUORESCENCE; HYDROGEN; DESIGN; PHOTOLUMINESCENCE; BEHAVIOR; DYES;
D O I
10.1080/02678292.2024.2381547
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Addressing the current challenge of high melting points and long pi-conjugated skeletons in luminescent nematic liquid crystals (LCs), this study explores the incorporation of push-pull dyes with biphenyl and tolane skeletons to extend fluorescence emission wavelengths into the visible light region. We synthesised push-pull-type biphenyl and tolane derivatives incorporating alkylamino groups as donors and cyano groups as acceptors. The thermal behaviour was investigated using optical polarisation microscopy, differential scanning calorimetry and X-ray diffraction. Notably, some molecules exhibited a nematic phase. The photophysical properties of the solution and solid states were also investigated. Furthermore, we formulated a room-temperature luminescent LC by blending several LCs. Importantly, the fluorescence in the nematic phase exhibited a red-shift compared to that observed in the solution and solid states. This study demonstrates the efficacy of the push-pull structure in the design of luminescent LCs. The findings of this study hold considerable implications for the development of advanced optoelectronic devices, particularly those requiring luminescent materials with tailored properties. [GRAPHICS]
引用
收藏
页码:2032 / 2045
页数:14
相关论文
共 76 条
[1]   Birefringence and photoluminescence properties of diphenylacetylene-based liquid crystal dimers [J].
Arakawa, Yuki ;
Sasaki, Shunsuke ;
Igawa, Kazunobu ;
Tokita, Masatoshi ;
Konishi, Gen-ichi ;
Tsuji, Hideto .
NEW JOURNAL OF CHEMISTRY, 2020, 44 (40) :17531-17541
[2]   Supramolecular hydrogen-bonded liquid crystals based on 4-n-alkylthiobenzoic acids and 4,4′-bipyridine: Their mesomorphic behavior with comparative study including alkyl and alkoxy counterparts [J].
Arakawa, Yuki ;
Sasaki, Yukito ;
Tsuji, Hideto .
JOURNAL OF MOLECULAR LIQUIDS, 2019, 280 :153-159
[3]   The design of liquid crystalline bistolane-based materials with extremely high birefringence [J].
Arakawa, Yuki ;
Kang, Sungmin ;
Tsuji, Hideto ;
Watanabe, Junji ;
Konishi, Gen-ichi .
RSC ADVANCES, 2016, 6 (95) :92845-92851
[4]   Diphenyltriacetylenes: novel nematic liquid crystal materials and analysis of their nematic phase-transition and birefringence behaviours [J].
Arakawa, Yuki ;
Kang, Sungmin ;
Nakajima, Shunpei ;
Sakajiri, Koichi ;
Cho, Yokan ;
Kawauchi, Susumu ;
Watanabe, Junji ;
Konishi, Gen-ichi .
JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (48) :8094-8102
[5]   Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties [J].
Arakawa, Yuki ;
Nakajima, Shunpei ;
Ishige, Ryohei ;
Uchimura, Makoto ;
Kang, Sungmin ;
Konishi, Gen-ichi ;
Watanabe, Junji .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (17) :8394-8398
[6]   Fluorescent liquid crystals with rod-shaped -conjugated hydrocarbon core [J].
Buchs, Jens ;
Gessner, Andre ;
Heyne, Benjamin ;
Janietz, Dietmar ;
Sawade, Hans .
LIQUID CRYSTALS, 2019, 46 (02) :281-298
[7]   Lasing in a three-dimensional photonic crystal of the liquid crystal blue phase II [J].
Cao, WY ;
Muñoz, A ;
Palffy-Muhoray, P ;
Taheri, B .
NATURE MATERIALS, 2002, 1 (02) :111-113
[8]   Synthesis, mesomorphic and fluorescent properties of stilbene-containing 1,3,4-oxadiazole compounds [J].
Chang, Xiao-Yong ;
Zhong, Wen-Yue ;
Han, Jie .
LIQUID CRYSTALS, 2023, 50 (11-12) :1709-1714
[9]   Chalcogen bonding and liquid crystallinity: Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB) [J].
Cruickshank, Ewan ;
Strachan, Grant J. ;
Storey, John Md ;
Imrie, Corrie T. .
JOURNAL OF MOLECULAR LIQUIDS, 2022, 346
[10]   Unlocking the potential of 2,1,3-benzoxadiazole-based luminescent liquid crystals [J].
da Silva, Fabricia Nunes ;
Silva, Eliane Oliveira ;
dos Santos, Gerson ;
Postacchini, Bruna B. ;
Cazati, Thiago ;
Bechtold, Ivan H. ;
Vieira, Andre Alexandre .
LIQUID CRYSTALS, 2023, 50 (11-12) :1688-1698