The synthesis of unsymmetrically substituted triphenylenes through controlled construction of the core and subsequent aromatic substitution reactions – a perspective and update

Cammidge, Andrew N.; Obi, Grace; Turner, Rebecca J.; Coles, Simon J.; Tizzard, Graham J.

doi:10.1080/02678292.2014.992054

Cited by 4 publications

(3 citation statements)

References 26 publications

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“…However, although bromination of pentaalkoxy triphenylene 8 occurs exclusively in the remaining β-site, nitration gives only α-substitution regardless of the temperature at which the reaction is performed. Indeed dibromination and dinitration of tetraalkoxytriphenylene 9 gives similar, surprising results (exclusive β-bromination and α-nitration respectively), Scheme .…”

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confidence: 82%

A π-Extended Donor–Acceptor–Donor Triphenylene Twin Linked via a Pyrazine Bridge

Xiao

Remiro‐Buenamañana

et al. 2015

Org. Lett.

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β-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophenone imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demonstrates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character.Discotic liquid crystals have attracted considerable attention from both a theoretical and applications point of view.1 Two general classes of liquid crystal phase are formed from discshaped molecules. Columnar phases are formed when the individual molecules stack on top of each other and the lattice arrangement of the resulting columns defines the sub-class of mesophase.2 Columnar phases are important because the stacking arrangement provides π-overlap in one direction only, leading to 1D conduction of charge and/or energy.3 Nematic phases, 4 where the molecules retain orientational order only, are much rarer, but also find important applications, most notably as optical compensating films in LCDs.

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confidence: 82%

A π-Extended Donor–Acceptor–Donor Triphenylene Twin Linked via a Pyrazine Bridge

Xiao

Remiro‐Buenamañana

et al. 2015

Org. Lett.

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“…Our group has made a number of contributions to this area, most recently concentrating on unsymmetrical, differentially substituted [7][8][9][10][11] and twinned systems. [12][13][14][15] Recent goals have been to explore structural parameters linked to discotic nematic mesophase formation [16] and to exploit the strong tendency of triphenylenebased systems to form mesophases to incorporate additional organic functionality into discotic phases. [17] Selected highlights include the intriguing nematic dehydroannulene twins 1, [12] pyrazine linked twin 2 [18] and mesogenic triphenylene-perylene-triphenylene triads 3.…”

Section: Introductionmentioning

confidence: 99%

“…Indeed, we recently reported straightforward access to such precursors. [15] The synthesis of lath-shaped twin 12 is shown in Scheme 1. Suzuki-Miyaura coupling [20] between 1,2-dibromo-4,5-bis(hexyloxy)benzene 5 [8] and benzene boronic acid 4 gave terphenyl 6.…”

Section: Introductionmentioning

confidence: 99%

A modified route to unsymmetrically substituted triphenylenes, new functionalised derivatives and twins, and the smallest reported triphenylene mesogen

et al. 2017

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We report the unexpected observation of columnar mesophase formation in a simple 2,7-dibromotetramethoxytriphenylene – by far the most lightly substituted discotic mesogen in this class. This derivative was prepared alongside the 3,6-dibromotriphenylene isomer to demonstrate an alternative, modified synthetic strategy that permits late-stage interchange of alkyl chain substituents. The new method is employed alongside the original route to deliver several new materials, including a conjugated ferrocene-triphenylene-ferrocene triad, a BODIPY-triphenylene-BODIPY triad and a new nematic twin linked through imine bridges

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Construction of Unsymmetrical Triphenylenes from Electron-Rich Biphenyls and Diaryliodonium Salts via Copper-Catalyzed Multiple C–H Arylation

Zhang

Peng

et al. 2018

Org. Lett.

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An efficient protocol to synthesize unsymmetrical triphenylenes from electron-rich biphenyls and diaryliodonium salts via Cu catalysis was developed. A variety of unsymmetrical triphenylenes with diversified functional groups were synthesized according to this method. This transformation went through multiple direct C-H arylations from easily produced starting materials with high step-economy. The gram-scale synthesis of triphenylenes and their facile transformation into diverse functional organic molecules were illustrated.

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The synthesis of unsymmetrically substituted triphenylenes through controlled construction of the core and subsequent aromatic substitution reactions – a perspective and update

Cited by 4 publications

References 26 publications

A π-Extended Donor–Acceptor–Donor Triphenylene Twin Linked via a Pyrazine Bridge

A π-Extended Donor–Acceptor–Donor Triphenylene Twin Linked via a Pyrazine Bridge

A modified route to unsymmetrically substituted triphenylenes, new functionalised derivatives and twins, and the smallest reported triphenylene mesogen

Construction of Unsymmetrical Triphenylenes from Electron-Rich Biphenyls and Diaryliodonium Salts via Copper-Catalyzed Multiple C–H Arylation

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