Abstract
Macrocyclic compounds have attracted tremendous attention for their superior performance in supramolecular recognition, catalysis, and host-guest interaction. With these admirable properties, macrocyclic compounds were used as modifiers for enhancing the sensitivity and selectivity of electrodes and optical sensors. The classic macrocyclic compounds, including crown ethers, cyclodextrins, calixarenes, cucurbiturils, and pillararenes, were employed as receptors for electrochemical and optical sensors to develop new analytical methods with the wilder detection range, lower detection limit, and better tolerance of interference. Macrocyclic molecules functionalized with nanomaterials, the small entities with dimensions in the nanoscale, realized the versatility and diversification of the nano-hybrid materials, which improved the capabilities of recognition and response with the combining characteristics of two components. Herein, this review focused on the development in the research field of hybridization of organic macrocycles with nanoparticles and their applications for chemosensors, aiming at both existing researchers in the field and who would like to enter into the research.
Keywords: Macrocyclic compound, supramolecular chemistry, chemosensor, nanomaterials, nano hybridization, molecular recognition, host-guest interaction.
Graphical Abstract
[http://dx.doi.org/10.1039/b809287g]
[http://dx.doi.org/10.1021/ar500116d] [PMID: 24785659]
[http://dx.doi.org/10.1021/acs.chemrev.5b00765] [PMID: 27337002]
[http://dx.doi.org/10.1039/C2CS35218D] [PMID: 22895524]
[http://dx.doi.org/10.1002/anie.198810211]
[http://dx.doi.org/10.1021/ol015778j] [PMID: 11388843]
[http://dx.doi.org/10.1021/ja029085p] [PMID: 14611211]
[http://dx.doi.org/10.1021/cr020080k] [PMID: 15137805]
[http://dx.doi.org/10.1039/C6CS00619A] [PMID: 27711665]
[http://dx.doi.org/10.1021/cr00014a009]
[http://dx.doi.org/10.1002/anie.199408031]
[http://dx.doi.org/10.1021/cr970012b] [PMID: 11848955]
[http://dx.doi.org/10.1021/cr970019t] [PMID: 11848948]
[http://dx.doi.org/10.1021/cr050576c] [PMID: 16522008]
[http://dx.doi.org/10.1002/anie.200701272] [PMID: 17526038]
[http://dx.doi.org/10.1021/ar00089a003]
[http://dx.doi.org/10.1016/S0040-4020(01)87580-3]
[http://dx.doi.org/10.1038/368229a0]
[http://dx.doi.org/10.1016/j.electacta.2008.02.085]
[http://dx.doi.org/10.1039/c0cs00005a] [PMID: 21321724]
[http://dx.doi.org/10.1021/jo00373a018]
[http://dx.doi.org/10.1021/ja993376p]
[http://dx.doi.org/10.1021/ja0319846] [PMID: 15125673]
[http://dx.doi.org/10.1021/ja052912c] [PMID: 16159293]
[http://dx.doi.org/10.1039/B603088M] [PMID: 17264929]
[http://dx.doi.org/10.1021/acs.chemrev.5b00341] [PMID: 26566008]
[http://dx.doi.org/10.1021/ar2003418] [PMID: 22551015]
[http://dx.doi.org/10.1039/C4CC03170A] [PMID: 25033095]
[http://dx.doi.org/10.1039/C2RA22123C]
[http://dx.doi.org/10.1039/C4CC06971D] [PMID: 25259721]
[http://dx.doi.org/10.1039/C7CC08365C] [PMID: 29205237]
[http://dx.doi.org/10.1016/j.snb.2017.03.163]
[http://dx.doi.org/10.1016/j.aca.2011.02.025] [PMID: 21458626]
[http://dx.doi.org/10.1039/c0cs00108b] [PMID: 21566801]
[http://dx.doi.org/10.1002/chem.201403107] [PMID: 25043786]
[http://dx.doi.org/10.1016/j.cclet.2013.04.014]
[http://dx.doi.org/10.1039/c3nr02176a] [PMID: 23832165]
[http://dx.doi.org/10.1039/b515806k] [PMID: 16582988]
[http://dx.doi.org/10.1039/c0cs00035c] [PMID: 20676412]
[http://dx.doi.org/10.1021/ac0202278] [PMID: 12090665]
[http://dx.doi.org/10.3390/s150100547] [PMID: 25558994]
[http://dx.doi.org/10.1002/elan.200704121]
[http://dx.doi.org/10.1016/j.snb.2013.02.036]
[http://dx.doi.org/10.1002/cbic.200700660] [PMID: 18247433]
[http://dx.doi.org/10.1016/j.talanta.2008.02.039] [PMID: 18585281]
[http://dx.doi.org/10.1016/j.elecom.2007.05.021]
[http://dx.doi.org/10.1016/j.talanta.2009.09.061] [PMID: 20152391]
[http://dx.doi.org/10.3390/s8010118] [PMID: 27879698]
[http://dx.doi.org/10.1002/elan.200390130]
[http://dx.doi.org/10.1021/jo301196m] [PMID: 22909394]
[http://dx.doi.org/10.1021/ac102922f] [PMID: 21302899]
[http://dx.doi.org/10.1002/adfm.200601202]
[http://dx.doi.org/10.1016/j.ab.2011.04.007] [PMID: 21530479]
[http://dx.doi.org/10.1039/an9628700083]
[http://dx.doi.org/10.1016/S0925-4005(98)00321-9]
[http://dx.doi.org/10.1016/j.aca.2013.03.041] [PMID: 23726094]
[http://dx.doi.org/10.1016/j.aca.2015.05.044] [PMID: 26320632]
[http://dx.doi.org/10.1038/363685a0]
[http://dx.doi.org/10.1021/cr970102g] [PMID: 11849010]
[http://dx.doi.org/10.1126/science.1158180] [PMID: 18511678]
[http://dx.doi.org/10.1038/nature04969] [PMID: 16855586]
[http://dx.doi.org/10.1039/c002690p] [PMID: 20623061]
[http://dx.doi.org/10.1039/c2nr11757f] [PMID: 22337209]
[http://dx.doi.org/10.1002/smll.201202896] [PMID: 23494883]
[http://dx.doi.org/10.1002/elan.201300304]
[http://dx.doi.org/10.1007/s00604-013-1022-7]
[http://dx.doi.org/10.1021/ac302747f] [PMID: 23140187]
[http://dx.doi.org/10.1039/c1cc11267h] [PMID: 21451857]
[http://dx.doi.org/10.1039/C2CC16481G] [PMID: 22179588]
[http://dx.doi.org/10.1039/c2cc33410k] [PMID: 22710921]
[http://dx.doi.org/10.1016/j.bios.2014.02.014] [PMID: 24594590]
[http://dx.doi.org/10.1016/j.electacta.2013.06.099]
[http://dx.doi.org/10.1039/b803851a] [PMID: 19082085]
[http://dx.doi.org/10.1039/C5OB01388G] [PMID: 26235312]
[http://dx.doi.org/10.1016/j.jcis.2017.08.086] [PMID: 28866461]
[http://dx.doi.org/10.1016/j.talanta.2012.09.016] [PMID: 23158302]
[http://dx.doi.org/10.1016/j.bios.2017.01.053] [PMID: 28160654]
[http://dx.doi.org/10.1039/C4TA05801A]
[http://dx.doi.org/10.1002/anie.201000902] [PMID: 20540128]
[http://dx.doi.org/10.1007/s00604-011-0758-1]
[http://dx.doi.org/10.1016/j.talanta.2014.03.048] [PMID: 24913851]
[http://dx.doi.org/10.1021/am403463p] [PMID: 24089695]
[http://dx.doi.org/10.1007/s11581-014-1343-5]
[http://dx.doi.org/10.1039/c2ay05892h]
[http://dx.doi.org/10.1039/C6RA10267K]
[http://dx.doi.org/10.1007/s00604-012-0928-9]
[http://dx.doi.org/10.1007/s00604-014-1287-5]
[http://dx.doi.org/10.1016/j.snb.2013.10.066]
[http://dx.doi.org/10.1002/smll.201503874] [PMID: 27151829]
[http://dx.doi.org/10.1016/j.microc.2019.104084]
[http://dx.doi.org/10.1016/j.snb.2014.08.012]
[http://dx.doi.org/10.1016/j.snb.2018.07.143]
[http://dx.doi.org/10.1007/s00216-019-02105-5] [PMID: 31598741]
[http://dx.doi.org/10.1016/j.snb.2016.05.148]
[http://dx.doi.org/10.1016/j.saa.2019.117176] [PMID: 31158763]
[http://dx.doi.org/10.3390/s18113927] [PMID: 30441777]
[http://dx.doi.org/10.1007/s10971-005-6621-2]
[http://dx.doi.org/10.1039/C5NR03395K] [PMID: 26255749]
[http://dx.doi.org/10.1007/s00204-015-1564-z] [PMID: 26140917]
[http://dx.doi.org/10.1039/b9pp00180h] [PMID: 20354643]
[http://dx.doi.org/10.1016/j.jhazmat.2013.11.067] [PMID: 24462971]
[http://dx.doi.org/10.1039/c3nr00580a] [PMID: 23632769]
[http://dx.doi.org/10.1016/j.chroma.2014.05.010] [PMID: 24856904]
[http://dx.doi.org/10.1016/j.jcis.2014.03.008] [PMID: 24767509]
[http://dx.doi.org/10.1016/j.microc.2019.03.060]
[http://dx.doi.org/10.1016/j.jpcs.2019.109145]
[http://dx.doi.org/10.1039/C9TB01020C] [PMID: 31432868]
[http://dx.doi.org/10.1016/j.snb.2019.127106]
[http://dx.doi.org/10.1016/j.jelechem.2019.113407]
[http://dx.doi.org/10.1016/j.talanta.2015.03.015] [PMID: 25966377]
[http://dx.doi.org/10.20964/110402612]
[http://dx.doi.org/10.1039/C8AY02648C]
[http://dx.doi.org/10.1016/j.snb.2017.08.162]
[http://dx.doi.org/10.1016/j.talanta.2012.07.040] [PMID: 22967631]