The synthesis and transition temperatures of some 4,4″-dialkyl- and 4,4″-alkoxyalkyl-1,1′ :4′,1″-terphenyls with 2,3- or 2′,3′-difluoro substituents and of their biphenyl analogues

Gray, G. W.; Hird, Michael; Lacey, D.; Toyne, Kenneth J.

doi:10.1039/p29890002041

Cited by 253 publications

(146 citation statements)

References 4 publications

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“…The present selectivity of CϪI over CϪBr groups in this reaction is very contribution describes the synthesis of a number of linear high. [8] In our own work, coupling at CϪBr has never been and kinked oligophenylene building blocks which carry not observed, even if CϪI was sterically more hindered, e.g. by only the functional group pattern required for repetitive an ortho-alkyl substitution.…”

Section: Introductionmentioning

confidence: 95%

Building Blocks for the Construction of Large Chloro-Functionalized, Hexagonal Oligophenylene Cycles

Hensel

Schlüter

1999

Eur. J. Org. Chem.

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The synthesis of a variety of kinked oligophenylene building blocks is described. The synthetic strategy is repetitive, utilizes the Suzuki cross‐coupling protocol, and involves potentially bifunctional building blocks (modules) which carry one functional group for coupling and one group which serves as place holder. After the coupling, the placeholder is converted into a coupling functionality for the next growth step. The building blocks also carry chloro‐substituents which are unaffected by all transformations. For one of the large building blocks it is shown that it actually can be cyclized into an oligophenylene macrocycle with a chloro‐substituent at each corner and a pair of hexyl chains at each side.

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Section: Introductionmentioning

confidence: 95%

Building Blocks for the Construction of Large Chloro-Functionalized, Hexagonal Oligophenylene Cycles

Hensel

Schlüter

1999

Eur. J. Org. Chem.

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“…4,7-Dibromo-2,1,3-benzothiadiazole (1), 23 3,6-dibromo-1,2-phenylenediamine (2), 24 1,4-dime-thylpiperazine-2,3-dione (3), 25 1-bromo-4-(octyloxy) benzene (4), 26 4,4'-bis(2-octyloxy)benzil (5), 25 5,8-Dibromo-2,3-bis-(4-octyloxyphenyl)quinoxaline (6), 27 2,3-Bis(4-octyloxyphenyl)-5,8-dithien-2-ly quinoxaline (7), 27 2,3-bis(4-octyloxyphenyl)-5,8-bis(5'-bromo-dithien-2-ly)quinoxaline (8), 27 and 5,5'-bis (trimethylstannyl)-2,2'-bithiophene 28 were prepared with previously described methods.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Quinoxaline-Based Thiophene Copolymers as Photoactive Layers in Organic Photovoltaic Cells

Choi¹,

Lee²,

Kim³

et al. 2011

Bulletin of the Korean Chemical Society

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A series of new quinoxaline-based thiophene copolymers (PQx2T, PQx4T, and PQx6T) was synthesized via Yamamoto and Stille coupling reactions. The Mws of PQx2T, PQx4T, and PQx6T were found to be 20,000, 12,000, and 29,000, with polydispersity indices of 2.0, 1.2, and 1.1, respectively. The UV-visible absorption spectra of the polymers showed two distinct absorption peaks in the ranges 350 -460 nm and 560 -600 nm, which arose from the π-π* transition of oligothiophene units and intramolecular charge transfer (ICT) between a quinoxaline acceptor and thiophene donor. The HOMO levels of the polymer ranged from -5.37 to -5.17 eV and the LUMO levels ranged from -3.67 to -3.45 eV. The electrochemical bandgaps of PQx2T, PQx4T, and PQx6T were 1.70, 1.71, and 1.72 eV, respectively, thus yielding low bandgap behavior. PQx2T, PQx4T, and PQx6T had open circuit voltages of 0.58, 0.42, and 0.47 V, and short circuit current densities of 2.9, 5.29 and 9.05 mA/cm 2 , respectively, when PC71BM was used as an acceptor. For the solar cells with PQx2T-PQx6T:PC71BM (1:3) blends, an increase in performance was observed in going from PQx2T to PQx6T. The power conversion efficiencies of PQx2T, PQx4T, and PQx6T devices were found to be 0.69%, 0.73%, and 1.80% under AM 1.5 G (100 mW/cm 2 ) illumination.

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“…Lacey and Mike Hird who made the most significant S C (*) material breakthrough through the development of the 2,3 substituted di-fluoro terphenyls and biphenyls [45].…”

Section: Implications For Flc Materials Designmentioning

confidence: 99%

On the biaxiality of smectic C and ferroelectric liquid crystals

Jones

2015

Liquid Crystals

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The synthesis and transition temperatures of some 4,4″-dialkyl- and 4,4″-alkoxyalkyl-1,1′ :4′,1″-terphenyls with 2,3- or 2′,3′-difluoro substituents and of their biphenyl analogues

Cited by 253 publications

References 4 publications

Building Blocks for the Construction of Large Chloro-Functionalized, Hexagonal Oligophenylene Cycles

Building Blocks for the Construction of Large Chloro-Functionalized, Hexagonal Oligophenylene Cycles

Synthesis and Characterization of Quinoxaline-Based Thiophene Copolymers as Photoactive Layers in Organic Photovoltaic Cells

On the biaxiality of smectic C and ferroelectric liquid crystals

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