杯吡咯是近年来一类新兴的超分子主体化合物,由于其独特的结构和理化性质,使得杯吡咯及其衍生物在识别金属离子、阴离子和中性小分子方面应用广泛。通过引入不同基团、改变其空腔大小得到的主体可以与不同大小、不同性质的客体分子相匹配,可作为敏感材料应用于离子选择电极、离子敏感场效应管、压电晶体、离子光导膜等多种类型的化学传感器上,对各种阴离子和中性分子的识别和检测。
Calixpyrrole was a new class of supramolecular host compounds in recent years.Because of its unique structure and physicochemical properties,calixpyrrole and its derivatives have been widely used in the recognition of metal ions,anions and neutral small molecules.By introducing different groups,the main body which can change the cavity size can match the guest molecules of different size and different nature,and can be used as the sensitive material in ion selective electrode,ion sensitive field effect transistor,piezoelectric crystal,ion photoconductive film And many other types of chemical sensors,for a variety of ions and neutral molecules identification and detection.
[1] Pedersen C J.Cyclic polyethers and their complexes with metal salts[J].Journal of the American Chemical Society,1967,89(26):7017-7036.
[2] Dey S,Pal K,Sarkar S.Synthesis of β-octabromocalix[4]pyrroles and conformational diversity in their acetone inclusion complexes[J].Tetrahedron Letters,2008,49(6):960-964.
[3] Dehaen W,Gale P A,Garcíagarrido S E,et al.Anion recognition by N-confused calix[4]pyrrole-α-carbaldehyde and its knoevenagel reaction derivatives[J].New Journal of Chemistry,2007,31(5):691-696.
[4] Boaz T,Alexer S,Moshe K,et al.ChemInform abstract:selective anion binding and solid-state host-guest chemistry of an extended cavity calix[6]pyrrole[J].Chemical Communications,2000,32(1):13-14.
[5] Yang W,Yin Z,Li Z,et al.A new acenaphthenequinone-based calix[4]pyrrole:synthesis,structure and anion binding study[J].Journal of Molecular Structure,2008,889(1/3):279-285.
[6] Giri N G,Chauhan S M S.Spectroscopic and spectrometric studies of anion recognition with calix[4]pyrroles in different reaction conditions[J].Spectrochimica Acta Part A Molecular & Biomolecular Spectroscopy,2009,74(1):297-304.
[7] Gale Philip A,Sessler Jonathan L,Král Vladimír,et al.Calix[4]pyrroles:old yet new anion-binding agents[J].Journal of the American Chemical Society,1996,118(21):5140-5141.
[8] Gale P A,Sessler J L,Allen W E,et al.Calix[4]pyrroles:c-rim substitution and tunability ofanion binding strength[J].Cheminform,1997,28(33):665-666.
[9] Sessler Jonathan L,Anzenbacher Avel,Miyaji Hidekazu,et al.Modified calix[4]pyrroles[J].Industrial & Engineering Chemistry Research,2000,39(10):3471-3478.
[10] Pavel Anzenbacher J,Karolina Jursíková A,Sessler J L.Second generation calixpyrrole anion sensors[J].J Am Chem Soc,2016,122(38):9350-9351.
[11] Lee C H,Na H K,Yoon D W,et al.Single side strapping:a new approach to fine tuning the anion recognition properties of calix[4]pyrroles[J].Journal of the American Chemical Society,2003,125(24):7301-7309.
[12] Ryuhei Nishiyabu,Minh A P,Wim Dehaen A,et al.Synthesis,structure,anion binding,and sensing by calix[4]pyrrole Isomers[J].Journal of the American Chemical Society,2006,128(35):11496-11504.
[13] Kim S K,Gross D E,Cho D G,et al.N-tosylpyrrolidine calix[4]pyrrole:synthesis and ion binding studies[J].Journal of Organic Chemistry,2011,76(76):1005-1012.
[14] Mahanta S P,Kumar B S,Baskaran S,et al.Colorimetric sensing of fluoride ion by new expanded calix[4]pyrrole through anion-π interaction[J].Organic Letters,2012,14(2):548-552.
[15] Zhou S,Wang H,Ping J,et al.Synthesis and characterization of organolanthanide complexes with a calix[4]-pyrrolyl ligand and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones[J].Organometallics,2012,31(5):1696-1702.
[16] 冯文玲.杯[4]吡咯及其衍生物对离子及离子对识别作用的分子模拟研究[D].扬州:扬州大学,2012.
[17] Nishiyabu R,Jr A P.Sensing of antipyretic carboxylates by simple chromogenic calix[4]pyrroles[J].Journal of the American Chemical Society,2005,127(23):8270-8281.
[18] Mulugeta E,He Q,Sareen D,et al.Recognition,sensing,and trapping of bicarbonate anions with a dicationic meso-bis(benzimidazolium) calix[4]pyrrole[J].Chem,2017,3(6):1008-1020.
[19] Pavel Anzenbacher,Tirsh A C,Hidekazu Miyaji,et al.Fluorinated calix[4]pyrrole and dipyrrolylquinoxaline:neutral anion receptors with augmented affinities and enhanced selectivities[J].Journal of the American Chemical Society,2000,122(42):10268-10272.
[20] Yoo J,Kim M S,Hong S J,et al.Selective sensing of anions with calix[4]pyrroles strapped with chromogenic dipyrrolylquinoxalines[J].Journal of Organic Chemistry,2009,74(3):1065-1069.
[21] Kim S K,Hong G L,Vargaszúñiga G I,et al.A fluorogenic calix[4]pyrrole with a small rigid strap showing different fluorescent responses to anions[J].Supramolecular Chemistry,2017,23(9):1-7.
[22] Allen W E,Gale P A,Brown C T,et al.Binding of neutral substrates by calix[4]pyrroles[J].J Am Chem Soc,1996,118(49):12471-12472.
[23] Bonomo L,Solari E,Toraman G,et al.ChemInform abstract:a cylindrical cavity with two different hydrogen-binding boundaries:the calix[4]arene skeleton screwed onto the meso-positions of the calix[4]pyrrole[J].Cheminform,2000,31(10):2413-2414.
[24] Baysak E,Yuvayapan S,Aydogan A,et al.Calix[4]pyrrole-decorated carbon nanotubes on paper for sensing acetone vapor[J].Sensors & Actuators B Chemical,2017,258:484-491.
[25] Fan J,Wang Z,Li Q,et al.Calix[4]pyrroles:highly selective stationary phases for gas chromatographic separations[J].Journal of Chromatography A,2014,1362:231-240.
[26] Gale P A,Gale P A,Twyman L J,et al.A colourimetric calix[4]pyrrole-4-nitrophenolate based anion sensor[J].Chemical Communications,1999,18(18):1851-1852.
[27] Sessler J L,An D,Cho W S,et al.Calix[2]bipyrrole[2]furan and calix[2]bipyrrole[2]thiophene:new pyrrolic receptors exhibiting a preference for carboxylate anions[J].Cheminform,2004,35(10):13646-13652.
[28] 黄晓梅.基于苯并吡喃腈的阴离子化学传感器及萘酰亚胺功能材料的研究[D].上海:华东理工大学,2011.
[29] Miyaji H,Jr P A,Sessler J L,et al.Anthracene-linked calix[4]pyrroles:fluorescent chemosensors for anions[J].Chemical Communications,1999,14(17):1723-1724.
[30] Ghorpade T K,Patri M,Mishra S P.Highly sensitive colorimetric and eluorometric anion sensors based on mono and di-calix[4]pyrrole substituted diketopyrrolopyrroles[J].Sensors & Actuators B Chemical,2015,225:428-435.
[31] Miyaji H,Sato W,Sessler J L.Naked-eye detection of anions in dichloromethane:colorimetric anion sensors based on calix[J].Angewandte Chemie International Edition,2010,39(10):1777-1780.
[32] Farinha Andreia S F,Fernandes Mónica R C,Tomé Augusto C.Chromogenic anion molecular probes based on β,β′-disubstituted calix[4]pyrroles[J].Sensors\s&\sactuators B(chemical),2014,200:332-338.
[33] Yeon Y,Leem S,Wagen C,et al.3-(Dicyanomethylidene)indan-1-one-functionalized calix[4]arene-calix[4]pyrrole hybrid:an ion-pair sensor for cesium salts[J].Organic Letters,2016,18(17):4396.
[34] Nielsen Kent A,Jeppesen Jan O,Levillain Eric,et al.Mono-tetrathiafulvalene calix[4]pyrrole in the electrochemical sensing of anions[J].Angewandte Chemie International Edition,2003,42(2):187-191.
[35] Thiampanya P,Muangsin N,Pulpoka B.Azocalix[4]arene strapped calix[4]pyrrole:a confirmable fluoride sensor[J].Organic Letters,2012,14(16):4050-4053.
[36] Aydogan A,Koca A,Sener M K,et al.EDOT-functionalized calix[4]pyrrole for the electrochemical sensing of fluoride in water[J].Organic Letters,2014,16(14):3764-3767.
基金资助
国家自然科学基金项目(51663012,51462021)