Highly dichroic benzo-2,1,3-thiadiazoledyes containing five linearly π-conjugated aromatic residues, with fluorescent emission ranging from green to red, in a liquid crystal guest–host system

Zhang, Xuelong; Yamaguchi, Rumiko; Moriyama, K.; Kadowaki, M.; Kobayashi, Tatsumasa; Ishi‐i, Tsutomu; Thiemann, Thies; Mataka, Shuntarō

doi:10.1039/b512493j

Cited by 69 publications

(33 citation statements)

References 30 publications

(23 reference statements)

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“…Copolymers S and L were prepared by the reaction sequences, which are presented in Schemes and . Compounds 1 ,55 2 ,55 3 ,34 4 ,56 and 5 57 were synthesized according to the literature. Moreover, 1,4‐divinyl‐2,5‐bis(hexyloxy)‐benzene54 was synthesized by Stille reaction53 of 1,4‐dibromo‐2,5‐bis(hexyloxy)‐benzene with tri‐ n ‐butyl(vinyl)tin.…”

Section: Resultsmentioning

confidence: 99%

Alternating phenylenevinylene copolymers with dithienbenzothiadiazole moieties: Synthesis, photophysical, and photovoltaic properties

Mikroyannidis

Stylianakis

Dong

et al. 2009

J of Applied Polymer Sci

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Two new soluble alternating phenylenevinylene copolymers S and L which contained dithienbenzothiadiazole moieties were synthesized by Heck coupling. The repeating unit of L was longer than that of S and contained two additional phenylene rings and two cyano-vinylene bonds. Both copolymers were stable up to about 350 C and afforded char yield of 52-66% at 800 C in N 2 . Their absorption spectra were broad and extended up to about 600 nm with a longer wavelength maximum at 447-502 nm and optical band gap of $ 2.0 eV. These copolymers emitted yellow light in solution with PL maximum at 551-580 nm and orange-red light in thin film with PL maximum at 588-661 nm. The emission maximum of L was considerably red-shifted relative to S. Photovoltaic cells based on S (or L) as donor and [6,6]-phenyl C61-butyric acid methyl ester as acceptor were investigated. V

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Section: Resultsmentioning

confidence: 99%

Alternating phenylenevinylene copolymers with dithienbenzothiadiazole moieties: Synthesis, photophysical, and photovoltaic properties

Mikroyannidis

Stylianakis

Dong

et al. 2009

J of Applied Polymer Sci

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“…Furthermore, similar as for Fluorescence in liquid crystal media has been extensively investigated in guest-host systems, in which a non-mesogenic fluorophore is dissolved in a thermotropic LC matrix. [52][53][54][55] However, the guest dye typically has a limited solubility in the host mesogen and, at high concentrations, often disrupts mesophase formation. [56,57] On the other hand, it is well established that the in-situ photopolymerisation of oriented reactive liquid crystals provides an excellent, versatile and facile method to produce anisotropic films.…”

Section: Thermal Propertiesmentioning

confidence: 99%

Coumarin-based emissive liquid crystals

Buchs

Gäbler²,

Janietz

et al. 2014

Liquid Crystals

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Calamitic luminophores are presented based on an elongated aryl-substituted coumarin core. The substitution pattern at terminal and lateral positions were systematically modified. The new compounds exhibit smectic C and/or nematic liquid crystalline phases. The chromophores show fluorescence in the blue spectral region. The benzopyranones are miscible with acrylate-substituted reactive nematic mesogens. Uniaxial orientation of the mixed systems was achieved by surface-assisted alignment on polyimide orientation layers. The film anisotropy was stabilised by subsequent photocrosslinking. The crosslinked oriented films display linear polarised photoluminescence upon isotropic excitation

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“…[25] The HOMO-LUMO energy gaps calculated from the onset of the experimentalo ptical absorption were 2.20 (4), and 2.46 eV (5), respectively. [26] The thermal properties of the new compounds were characterizedb yt hermogravimetric analysis( TGA) and differential scanningc alorimetry (DSC). Weight losses ( % 5%)w ereo bserved at temperatures higher than 351 and 368 8Cf or 4 and 5,r espectively ( Figure S1 in the Supporting Information).…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Benzothiadiazole‐Based Small‐Molecule Semiconductors for Organic Thin‐Film Transistors and Complementary‐like Inverters

et al. 2017

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New benzothiadiazole derivatives, 4,7‐bis(5‐phenylthiophen‐2‐yl)benzo[c][1,2,5]thiadiazole (PT‐BTD) and 4,7‐bis[4‐(thiophen‐2‐yl)phenyl]benzo[c][1,2,5]thiadiazole (TP‐BTD), were synthesized and characterized as small‐molecule organic semiconductors for organic thin‐film transistors (OTFTs) and complementary inverters. The thermal, optical, and electrochemical properties of the new compounds were fully characterized. Vacuum‐deposition and solution‐shearing methods were used to fabricate thin films based on these compounds. Thin films based on PT‐BTD exhibited p‐channel characteristics with hole mobilities as high as 0.10 cm2 V−1 s−1 and current on/off ratios >107 for top‐contact/bottom‐gate OTFT devices. With an optimized blending ratio of PT‐BTD and the representative n‐channel semiconductor N,N′‐1H,1H‐perfluorobutyl dicyanoperylenediimide, bulk heterojunction ambipolar transistors were fabricated with balanced hole and electron mobilities of 0.10 and 0.07 cm2 V−1 s−1, respectively. Furthermore, a complementary‐like inverter was fabricated using ambipolar thin‐film transistors, which showed a high voltage gain of 84.

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Highly dichroic benzo-2,1,3-thiadiazoledyes containing five linearly π-conjugated aromatic residues, with fluorescent emission ranging from green to red, in a liquid crystal guest–host system

Cited by 69 publications

References 30 publications

Alternating phenylenevinylene copolymers with dithienbenzothiadiazole moieties: Synthesis, photophysical, and photovoltaic properties

Alternating phenylenevinylene copolymers with dithienbenzothiadiazole moieties: Synthesis, photophysical, and photovoltaic properties

Coumarin-based emissive liquid crystals

Benzothiadiazole‐Based Small‐Molecule Semiconductors for Organic Thin‐Film Transistors and Complementary‐like Inverters

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