

浏览全部资源
扫码关注微信
1.桂林理工大学 化学与生物工程学院, 广西 桂林 541004
2.北部湾大学 石油与化工学院, 广西 钦州 535011
Received:14 May 2019,
Accepted:03 September 2019,
Published:05 November 2019
移动端阅览
Xiang-fei KONG, Jun LI, Jian-wen YU, et al. Progress in intermolecular hydrogen bond-assembled supramolecular liquid crystals[J]. Chinese journal of liquid crystals and displays, 2019, 34(11): 1037-1054.
Xiang-fei KONG, Jun LI, Jian-wen YU, et al. Progress in intermolecular hydrogen bond-assembled supramolecular liquid crystals[J]. Chinese journal of liquid crystals and displays, 2019, 34(11): 1037-1054. DOI: 10.3788/YJYXS20193411.1037.
介绍了近十几年来典型的氢键组装的超分子液晶材料的组装方法和分子结构,对比其光电性能和自组装特点,并对其在光电器件方面的应用进行展望。这类材料依据氢键组装的方式和分子结构主要分为两大类:结构封闭型和结构开放型。与后者相比,前者具有易于结构修饰和易于精确调控性能的特点。但两者内部的分子结构变化时,组装的超分子液晶材料的性能均受到显著影响。分子间氢键作用组装的超分子液晶材料具有高度有序性和可精确调控性,因此作为新型材料在有机光电器件和纳米器件等领域具有广阔的应用前景。
In this paper
the typical hydrogen bond-assembled supramolecular liquid crystal materials are summarized over the past decade. Their preparation methods and molecular structures are presented
and their photoelectric properties and self-assembly characteristics are compared
as well as their applications in optoelectronic devices are prospected. According to the kinds of hydrogen bonds and the molecular structures
these materials are mainly divided into two categories:closed-type and open-type structures. Compared with the latter
the former has the characteristics of easy structural modification and precise structure control. However
the properties of all these assembled supramolecular liquid crystal materials are significantly affected by the changes of their internal molecular structure. These materials assembled by intermolecular hydrogen bonding are highly ordered and their molecular structures are precisely controllable. As a novel material
it has broad application prospects in the field of organic photoelectronic devices and nanodevices.
HUGGINS M L. Hydrogen bridges in organic compounds[J]. The Journal of Organic Chemistry , 1936, 1(5):407-456.
BERNAL J D, MEGAW H D. The function of hydrogen in intermolecular forces[J]. Proceedings of the Royal Society A : Mathematical , Physical and Engineering Sciences , 1935, 151(873):384-420.
LIANG T, WU Y, TAN S, et al . Enhancing proton conduction via doping of supramolecular liquid crystals (4-alkoxybenzoic acids) with imidazole[J]. Chemical Physics Letters , 2015, 637:22-25.
LUGGERJ A M, SIJBESMA R P. Easily accessible thermotropic hydrogen-bonded columnar discotic liquid crystals from fatty acid-tris-benzoimidazolyl benzene complexes[J]. Chemistry Open , 2016, 5(6):580-585.
LEE J H. Supramolecular discotic nematic liquid crystals built through simple hydrogen bonding between 1, 3, 5-tris(4-hydroxyphenyl)benzene and stilbazole derivatives[J]. Molecular Crystals and Liquid Crystals , 2016, 635(1):133-138.
XU X Y, ZHANG B Y, WANG L X, et al . Effect of the site of hydrogen-bonding on the liquid crystalline behaviour of supramolecular complexes[J]. Liquid Crystals , 2009, 36(12):1365-1372.
HE W L, GU H, ZHAO P, et al .Synthesis and mesophase behaviour of branched azobenzene-based supramolecular hydrogen-bonded liquid crystals[J]. Liquid Crystal , 2017, 44(3):593-602.
MAHALINGAM T, VENKATACHALAM T, JAYAPRAKASAM R, et al .Structural and thermo-optic studies on linear double hydrogen bonded ferroelectric liquid crystal homologous series[J]. Molecular Crystals and Liquid Crystals , 2016, 641(1):10-24.
KIM H J, CHO S, PARK J S. Columnar liquid crystalline self-assembly of hydrogen-bonded rod-coil diblock complexes created from pyrazole/benzoic acid derivatives[J]. Bulletin of the Korean Chemical Society , 2015, 36(11):2740-2745.
KATO T, MIZOSHITA N, KISHIMOTO K. Functional liquid-crystalline assemblies:self-organized soft materials[J]. Angewandte Chemie International Edition , 2006, 45(1):38-68.
LIU M H, ZHANG L, WANG T Y. Supramolecular chirality in self-assembled systems[J]. Chemical Reviews , 2015, 115(15):7304-7397.
BISOYI H K, KUMAR S. Liquid-crystal nanoscience:an emerging avenue of soft self-assembly[J]. Chemical Society Reviews , 2011, 40(1):306-319.
王冉, 李向阳. BTAs类成核剂N, N', N″-三环己基-1, 3, 5-苯酰胺的合成研究[J].塑料助剂, 2018(1):17-20, 31.
WANG R, LI X Y. Study on the synthesis of BTAs nucleating agents 1, 3, 5-benzenetricarboxylic acid[J]. Plastic Additives , 2018(1):17-20, 31. (in Chinese)
李莉.均苯三甲酰胺键联三卟啉对手性单醇的识别研究[D].苏州: 苏州大学, 2016. http://cdmd.cnki.com.cn/Article/CDMD-10285-1016220224.htm
LI L.Chiral recognition of monoalcohols by benzene tricarboxamide-linked trisporphyrinates[D]. Suzhou: Soochow University, 2016. (in Chinese)
张跃飞, 周培章, 杨鑫, 等.脂肪族C4取代1, 3, 5-苯三甲酰胺的合成及对聚丙烯结晶熔融行为的影响[J].塑料工业, 2017, 45(5):120-123, 77.
ZHANG Y F, ZHOU P Z, YANG X, et al . Synthesis of aliphatic C4 substituted 1, 3, 5-benzenictrisamides and effects on crystallization and melting behaviors of polypropylene[J]. China Plastics Industry , 2017, 45(5):120-123, 77. (in Chinese)
INVERNIZZI C, DALVIT C, STOECKLI-EVANS H, et al . Synthesis and NMR spectroscopic study of the self-aggregation of 2-substituted benzene-1, 3, 5-tricarboxamides[J] . European Journal of Organic Chemistry , 2015, 2015(23):5115-5127.
FAGNANI D E, MEESE JR M J, ABBOUD K A, et al . Homochiral[2.2]paracyclophane self-assembly promoted by transannular hydrogen bonding[J] . Angewandte Chemie International Edition , 2016, 55(36):10726-10731.
DESMARCHELIER A, ALVARENGA B G, CAUMES X, et al . Tuning the nature and stability of self-assemblies formed by ester benzene 1, 3, 5-tricarboxamides:the crucial role played by the substituents[J]. Soft Matter , 2016, 12(37):7824-7838.
MOLLA R M, GHOSH S. Structural variations on self-assembly and macroscopic properties of 1, 4, 5, 8-naphthalene-diimide chromophores[J]. Chemistry of Materials , 2011, 23(1):95-105.
SOBERATS B, HECHT M, WÜRTHNER F. Diketopyrrolopyrrole columnar liquid-crystalline assembly directed by quadruple hydrogen bonds[J]. Angewandte Chemie International Edition , 2017, 56(36):10771-10774.
HECHT M, SOBERATS B, ZHU J, et al . Anisotropic microfibres of a liquid-crystalline diketopyrrolopyrrole by self-assembly-assisted electrospinning[J]. Nanoscale Horizons , 2019, 4(1):169-174.
GRZYBOWSKI M, GRYKO D T. Diketopyrrolopyrroles:synthesis, reactivity, and optical properties[J]. Advanced Optical Materials , 2015, 3(3):280-320.
STOLTE M, SURARU S L, DIEMER P, et al . Diketopyrrolopyrrole organic thin-film transistors:impact of alkyl substituents and tolerance of ethylhexyl stereoisomers[J]. Advanced Functional Materials , 2016, 26(41):7415-7422.
GŁOWACKI E D, COSKUN H, BLOOD-FORSYTHE M A, et al . Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors[J]. Organic Electronics , 2014, 15(12):3521-3528.
LI W W, HENDRIKS K H, WIENK M M, et al . Diketopyrrolopyrrole polymers for organic solar cells[J]. Accounts of Chemical Research , 2016, 49(1):78-85.
PICKAERT G, DOUCE L, ZIESSEL R, et al .Mesomorphic phenanthroline derivatives:novel architectures based on hydrogen bonding[J]. Chemical Communications , 2002(15):1584-1585.
WANG K, BOHRA H, GONÇALVES R A, et al . Multiscale self-assembly of a phenyl-flanked diketopyrrolopyrrole derivative:a solution-processable building block for π-conjugated supramolecular polymers[J]. Langmuir , 2019, 35(16):5626-5634.
KAAFARANI B R. Discotic liquid crystals for opto-electronic applications[J]. Chemistry of Materials , 2011, 23(3):378-396.
FLEISCHMANN E K, ZENTEL R. Liquid-crystalline ordering as a concept in materials science:from semiconductors to stimuli-responsive devices[J]. Angewandte Chemie International Edition , 2013, 52(34):8810-8827.
WÖHRLE T, WURZBACH I, KIRRES J, et al . Discotic liquid crystals[J]. Chemical Reviews , 2016, 116(3):1139-1241.
SUÁREZ M, LEHN J M, ZIMMERMAN S C, et al . Supramolecular liquid crystals. Self-assembly of a trimeric supramolecular disk and its self-organization into a columnar discotic mesophase[J]. Journal of the American Chemical Society , 1998, 120(37):9526-9532.
BLANCO H, IGUARBE V, BARBERÁ J, et al . Supramolecular columnar liquid crystals with tapered-shape simple pyrazoles obtained by efficient Henry/Michael reactions[J]. Chemistry - A European Journal , 2016, 22(14):4924-4930.
VINAYAKUMARA D R, KUMAR S, ADHIKARI A V. Supramolecular columnar self-assembly of wedge-shaped rhodanine based dyes:synthesis and optoelectronic properties[J]. Journal of Molecular Liquids , 2019, 274:215-222.
FOSTER E J, LAVIGUEUR C, KE Y C, et al . Self-assembly of hydrogen-bonded molecules:discotic and elliptical mesogens[J]. Journal of Materials Chemistry , 2005, 15(37):4062-4068.
LAVIGUEUR C, FOSTER E J, WILLIAMS V E. Self-assembly of discotic mesogens in solution and in liquid crystalline phases:effects of substituent position and hydrogen bonding[J]. Journal of the American Chemical Society , 2008, 130(35):11791-11800.
FERINGÁN B, ROMERO P, SERRANO J L, et al . Supramolecular columnar liquid crystals formed by hydrogen bonding between a clicked star-shaped s -triazine and benzoic acids[J]. Chemistry - A European Journal , 2015, 21(24):8859-8866.
JURIČEK M, KOUWER P H J, ROWAN A E. Triazole:a unique building block for the construction of functional materials[J]. Chemical Communications , 2011, 47(31):8740-8749.
SCHULZE B, SCHUBERT U S. Beyond click chemistry-supramolecular interactions of 1, 2, 3-triazoles[J]. Chemical Society Reviews , 2014, 43(8):2522-2571.
KATO T, YASUDA T, KAMIKAWA Y, et al . Self-assembly of functional columnar liquid crystals[J]. Chemical Communications , 2009(7):729-739.
TSCHIERSKE C. Development of structural complexity by liquid-crystal self-assembly[J]. Angewandte Chemie International Edition , 2013, 52(34):8828-8878.
GONZÁLEZ-RODRÍGUEZ D, SCHENNING A P H J. Hydrogen-bonded supramolecular π-functional materials[J]. Chemistry of Materials , 2011, 23(3):310-325.
GUO X L, LIU Y H, WANG L, et al . Hydrogen-bonding induced melamine-core supramolecular discotic liquid crystals[J]. Journal of Materials Chemistry C , 2017, 5(35):9165-9173.
LEE S J, JHO J Y, LEE J H. Supramolecular discotic columnar liquid crystals built through single hydrogen bonding between carboxylic acid and pyridine moieties[J]. Molecular Crystals and Liquid Crystals , 2015, 621(1):169-174.
LEE S J, YOU M K, LEE S W, et al . Star-shaped supramolecular liquid crystals formed by hydrogen bonding between phloroglucinol and stilbazole derivatives with different molecular shapes[J]. Liquid Crystals , 2011, 38(10):1289-1299.
LEE J H, JANG I, HWANG S H, et al . Self-assembled discotic nematic liquid crystals formed by simple hydrogen bonding between phenol and pyridine moieties[J]. Liquid Crystals , 2012, 39(8):973-981.
LEE S J, LEE J, LEE S W, et al . Photoluminescent supramolecular liquid crystals formed by hydrogen bonding of non-mesogenic donor and acceptors[J]. Journal of Industrial and Engineering Chemistry , 2012, 18(2):767-774.
LEE J W, LEE S J, JHO J Y, et al . Preparation and photoluminescent properties of hydrogen-bonded discotic liquid crystals[J]. Molecular Crystals and Liquid Crystals , 2015, 621(1):70-75.
PFLETSCHER M, HÖLSCHER S, WÖLPER C, et al . Structure-property relationships in hydrogen-bonded liquid crystals[J]. Chemistry of Materials , 2017, 29(19):8462-8471.
GIESE M, KRAPPITZ T, DONG R Y, et al . Tuning the photonic properties of chiral nematic mesoporous organosilica with hydrogen-bonded liquid-crystalline assemblies[J]. Journal of Materials Chemistry C , 2015, 3(7):1537-1545.
DONG R J, ZHOU Y F, HUANG X H, et al . Functional supramolecular polymers for biomedical applications[J]. Advanced Materials , 2015, 27(3):498-526.
YANG Y, URBAN M W. Self-healing polymeric materials[J]. Chemical Society Reviews , 2013, 42(17):7446-7467.
LIU K, KANG Y T, WANG Z Q, et al .25th anniversary article:reversible and adaptive functional supramolecular materials:″noncovalent interaction″ matters[J]. Advanced Materials , 2013, 25(39):5530-5548.
YAN X Z, WANG F, ZHENG B, et al .Stimuli-responsive supramolecular polymeric materials[J]. Chemical Society Reviews , 2012, 41(18):6042-6065.
KIHARA H, KATO T, URYU T, et al . Supramolecular liquid-crystalline networks built by self-assembly of multifunctional hydrogen-bonding molecules[J]. Chemistry of Materials , 1996, 8(4):961-968.
姚威.含分子间氢键的超分子的合成及液晶性质研究[D].桂林: 桂林理工大学, 2018.
YAO W. Investigation on synthesis and properties of supermolecules with intermolecular hydrogen bonds[D]. Guilin: Guilin University of Technology, 2018. (in Chinese)
MITANI M, YOSHIO M, KATO T.Tuning of luminescence color of π-conjugated liquid crystals through co-assembly with ionic liquids[J]. Journal of Materials Chemistry C , 2017, 5(38):9972-9978.
GOODBY J W, COLLINGS P J, KATO T, et al . Handbook of Liquid Crystals [M]. Weinheim, Germany:John Wiley & Sons, 2014.
GOODBY J W, SAEZ I M, COWLING S J, et al . Transmission and amplification of information and properties in nanostructured liquid crystals[J]. Angewandte Chemie International Edition , 2008, 47(15):2754-2787.
LV C, TAKEDA T, HOSHINO N, et al . Tubular and lamellar hydrogen-bonding molecular assemblies of isophthalic acid derivatives bearing a -CONHC n H 2n +1 chain[J]. RSC Advances , 2018, 8(39):22250-22258.
SACCONE M, KUNTZE K, AHMED Z, et al . ortho -Fluorination of azophenols increases the mesophase stability of photoresponsive hydrogen-bonded liquid crystals[J]. Journal of Materials Chemistry C , 2018, 6(37):9958-9963.
UCHIDA J, KATO T. Liquid-crystalline fork-like dendrons[J]. Liquid Crystals , 2017, 44(12/13):1816-1829.
ROOHNIKAN M, LINDNER-D'ADDARIO M, TOADER V, et al .Mechanochemical nanoparticle functionalization for liquid crystal nanocomposites based on COOH-pyridine heterosynthons[J]. Journal of Materials Chemistry C , 2018, 6(7):1789-1796.
MULDER D J, LIANG T, XU Y F, et al . Proton conductive cationic nanoporous polymers based on smectic liquid crystal hydrogen-bonded heterodimers[J]. Journal of Materials Chemistry C , 2018, 6(18):5018-5024.
0
Views
32
下载量
1
CSCD
Publicity Resources
Related Articles
Related Author
Related Institution
京公网安备11010802024621