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·1756· 精细化工 FINE CHEMICALS 第 39 卷

[3] KAWAGOE F, MOTOTANI S, KITTAKA A. Design and synthesis [23] ADAM D, SCHUHMACHER P, SIMMERER J, et al. Fast
of fluoro analogues of vitamin D[J]. International Journal of photoconduction in the highly ordered columnar phase of a discotic
Molecular Sciences, 2021, 22(15): 8191-8216. liquid-crystal[J]. Nature, 1994, 371(6493): 141-143.
[4] AGOPIAN J C, TÉRAUBE O, CHARLET K, et al. A review about [24] ZAMIR S, POUPKO R, LU Z B, et al. Molecular ordering and
the fluorination and oxyfluorination of carbon fibres[J]. Journal of dynamics in the columnar mesophase of a new dimeric discotic
Fluorine Chemistry, 2021, 251: 109887. liquid-crystal as studied by X ray diffraction and deuterium NMR[J].
[5] KRUPPKE I, SCHEFFLER C, SIMON F, et al. Surface treatment of Journal of the American Chemical Society, 1994, 116(5): 1973-1980.
carbon fibers by oxy-fluorination[J]. Materials, 2019, 12(4): 565-583. [25] BODEN N, BUSHBY R J, CAMMIDGE A N, et al. Alpha-
[6] WANG J H, FU S Q, LIU X H, et al. Multifunctional fluorinated halogenation of triphenylene-based discotic liquid crystals: Towards
ammonium salt for high-performance all-inorganic CsPbI 2Br a chiral nucleus[J]. Journal of Materials Chemistry, 1997, 7(4): 601-605.
perovskite solar cells with efficiency of 16. 29%[J]. Journal of Alloys [26] ZHAO K Q, GAO Y, YU W H, et al. Discogens possessing aryl side
and Compounds, 2022, 891: 161971. groups synthesized by Suzuki coupling of triphenylene triflates and
[7] XIA L, MIAO H, ZHANG C F, et al. Review—Recent advances in their self-organization behavior[J]. European Journal of Organic
non-aqueous liquid electrolytes containing fluorinated compounds Chemistry, 2016, (16): 2802-2814.
for high energy density lithium-ion batteries[J]. Energy Storage [27] ZHAO K Q, JING M, AN L L, et al. Facile Transformation of
Materials, 2021, 38: 542-570. 1-aryltriphenylenes into dibenzo[fg, op]tetracenes by
[8] MADHU M, RAMAKRISHNAN R, VIJAY V, et al. Free charge intramolecularscholl cyclodehydrogenation: Synthesis, self-assembly,
carriers in homo-sorted Pi-stacks of donor-acceptor conjugates[J]. and charge carrier mobility of large π-extended discogens[J]. Journal
Chemical Reviews, 2021, 121(13): 8234-8284. of Materials Chemistry C, 2017, 5(3): 669-682.
[9] ABHILASH T K, VARGHESE H, CZERWIŃSKI M, et al. Probing [28] ZHAO K Q, DU J Q, LONG X H, et al. Design of
the effect of chiral dopant fluorination on dielectric and electro-optical janustriphenylenemesogens: Facile synthesis, mesomorphism,
properties of the ferroelectric liquid crystalline mixture[J]. Journal of photoluminescence, and semiconductivity[J]. Dyes and Pigments,
Molecular Liquids, 2021, 341: 117392. 2017, 143: 252-260.
[10] FOUAD F S, KHAIRUDDEAN M, TWIEG R J. Diphenyl-1, 3, [29] GUO J (郭剑), LI Z Q (李正强), ZHANG X (张兴). Liquid crystal
4-oxadiazoles: Synthesis and influence of side chain semifluorination compounds, and preparation method and application thereof:
and lateral ring fluorination on liquid crystalline properties[J]. CN104387398B[P]. 2018-04-24.
Molecular Crystals and Liquid Crystals, 2022, 732(1): 64-75. [30] LI Z M, ZHANG G, LI D S, et al. Polyamides containing thiadiazole
[11] KATARIYA K D, NAKUM K J, HAGAR M. New fluorinated units: Synthesis and optical properties[J]. Chinese Journal of Polymer
azo/Schiff base liquid crystals: Synthesis, characterisation, mesomorphic Science, 2014, 32(3): 292-304.
study and DFT calculations[J]. Liquid Crystals, 2022, 49(3): 312-326. [31] ZHANG G, BAI D T, LI D S, et al. Synthesis and properties of
[12] MENG F B (孟凡宝), LIAN J (廉娇), GAO Y M (高永梅). polyamides derived from 4, 6-bis(4-chloroformylphenylthio)pyrimidine
Advances in fluorinated liquid crystals[J]. Progress in Chemistry (化 and 3, 6-bis(4-chloroformylphenylthio)pyridazine[J]. Polymer
学进展), 2008, 20(4): 499-507. International, 2013, 62(9): 1358-1367.
[13] FOSTER E J, JONES R B, LAVIGUEUR C, et al. Structural factors [32] YARDLEY R E, PAQUETTE J A, TAING H, et al. Stabilization of
controlling the self-assembly of columnar[J]. Journal of the American columnar liquid crystal phases via arene-perfluoroareneinteractions[J].
Chemical Society, 2006, 128: 8569-8574. Organic Letters, 2019, 21(24): 10102-10105.
[14] PAQUETTE J A, YARDLEY C J, PSUTKA K M, et al. Dibenz[a, [33] CLAESSENS C G, BLAU W J, COOK M, et al. Phthalocyanines and
c]anthracene derivatives exhibiting columnar mesophases over broad phthalocyanine analogues: The quest for applicable optical properties
temperature ranges[J]. Chemical Communications, 2012, 48(66): [J]. Monatshefte für Chemie-Chemical Monthly, 2001, 132(1): 3-11.
8210-8212. [34] WOHRLE D, SCHNURPFEIL G, KNOTHE G. Efficient synthesis of
[15] PAQUETTE J A, PSUTKA K M, YARDLEY C J, et al. Probing the phthalocyanines and related macrocyclic-compounds in the presence
structural features that influence the mesomorphic properties of of organic-bases[J]. Dyes and Pigments, 1992, 18(2): 91-102.
substituted dibenz[a, c]anthracenes[J]. Canadian Journal of Chemistry, [35] CLAESSENS C G, HAHN U, TORRES T. Phthalocyanines: From
2017, 95(4): 399-409. outstanding electronic properties to emerging applications[J]. Chemical
[16] DAHN U, ERDELEN C, RINGSDORF H, et al. Fluoroalkylateddiscotic Record, 2008, 8(2): 75-97.
liquid-crystals[J]. Liquid Crystals, 1995, 19(6): 759-764. [36] ARMSTRONG N R. Phthalocyanines and porphyrins as materials[J].
[17] WILLIAMS J H. The molecular electric. Quadrupole-moment and Journal of Porphyrins and Phthalocyanines, 2000, 4(4): 414-417.
solid-state architecture[J]. Accounts of Chemical Research, 1993, [37] AHMIDA M, LAROCQUE R, AHMED M S, et al. Halide effect in
26(11): 593-598. electron rich and deficient discotic phthalocyanines[J]. Journal of
[18] SMITH C E, SMITH P S, THOMAS R L, et al. Arene-perfluoroarene Materials Chemistry, 2010, 20(7): 1292-1303.
interactions in crystal engineering: Structural preferences in [38] TAKAGI A, MIZUTANI T. Control of the molecular packing of
polyfluorinatedtolans[J]. Journal of Materials Chemistry, 2004, chloroboron( Ⅲ ) and fluoroboron( Ⅲ ) subnaphthalocyanines by
14(3): 413-420. designing peripheral substituents[J]. RSC Advances, 2017, 7(85):
[19] REICHENBACHER K, SUSS H I, HULLIGER J. Fluorine in crystal 54235-54245.
engineering-"The little atom that could"[J]. Chemical Society [39] CONCELLÓN A, LU R Q, YOSHINAGA K, et al. Electric-field-
Reviews, 2005, 34(1): 22-30. induced chirality in columnar liquid crystals[J]. Journal of the
[20] COATES G W, DUNN A R, HENLING L M, et al. Phenyl- American Chemical Society, 2021, 143(24): 9260-9266.
perfluorophenyl stacking interactions: A new strategy for supermolecule [40] MIYAKE Y, FUJII A, OZAKI M, et al. Charged carrier mobility
construction[J]. Angewandte Chemie International Edition, 1997, study in colh mesophase of perfluoroalkylated triphenylene derivatives
36(3): 248-251. [J]. Molecular Crystals and Liquid Crystals, 2010, 516(1): 246-252.
[21] RIPPY K C, DEWEERD N J, KUVYCHKO I V, et al. Fluorination- [41] CHEN H M, ZHAO K Q, WANG L, et al. Synthesis and
induced evolution of columnar packing in fluoroustriphenylenes and mesomorphism of triphenylene discotic liquid crystals containing
benzotriphenylenes[J]. ChemPlusChem, 2018, 83(12): 1067-1077. fluorinated chains[J]. Soft Materials, 2011, 9(4): 359-381.
[22] MAITI B, WANG K L, BHANDARI S, et al. Enhancing charge [42] CHAVEZ F V, SEBASTIAO P J, MIYAKE Y, et al. Dynamics of
mobilities in selectively fluorinated oligophenyl organic semiconductors: discotic fluoroalkylated triphenylene molecules studied by proton
A design approach based on experimental and computational NMR relaxometry[J]. Journal of Physical Chemistry B, 2012, 116(8):
perspectives[J]. Journal of Materials Chemistry C, 2019, 7(13): 2339-2346.
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