Abstract
Differentiation of enantiomers remains one of the most attractive and important research areas in analytical chemistry due to its impact on pharmaceutical, chemical, biotechnology, and food industries. For a long time chiral separation techniques, such as high performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE), have represented the gold standard for the separation and determination of enantiomers. These techniques, besides being time consuming and expensive, are also not suitable for real time analysis. Therefore, the development of fast and reliable chiral sensors remains a challenge to achieve on-line analysis of enantiomers in both gas and liquid samples. The scope of this chapter is to provide an overview on the basic functioning principles, as well as on the performance level, of solid-state sensing devices for enantiomers differentiation. Particular attention is paid to work providing a set of analytical figures of merit (sensitivity, repeatability, reproducibility, limit-of-detection, etc.) as well as to studies involving miniaturized (or miniaturizable) analytical devices that can deliver real-time, on-line, and label-free information on chiral compounds.
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Abbreviations
- AFM:
-
Atomic force microscopy
- Ala:
-
Alanine
- Apt:
-
Aptamer
- APTES:
-
3-Aminopropyltriethoxysilane
- Asp:
-
Aspartic acid
- CD:
-
Cyclodextrins
- CLEP:
-
Chiral ligand exchange potentiometry
- CSA:
-
Camphor sulfonic acid
- CV:
-
Cyclic voltammetry
- Cy:
-
Cysteine
- DOPA:
-
Dopamine
- DPV:
-
Differential pulse voltammetry
- EIS:
-
Electrochemical impedance spectroscopy
- GC:
-
Gas chromatography
- Glu:
-
Glutamic acid
- GSA:
-
Goat serum albumin
- Hcy:
-
Homocysteine
- His:
-
Histidine
- HSA:
-
Human serum albumin
- ISE:
-
Ion-selective electrode
- ISFET:
-
Ion-selective field effect transistor
- ITO:
-
Indium tin oxide
- MA:
-
Mandelic acid
- MIP:
-
Molecular imprinted polymer
- MPTMS:
-
(3-Mercaptopropyl)trimethoxysilane
- OCD:
-
Optical circular dichroism
- OFET:
-
Organic film effect transistor
- OTS:
-
Octadecyltrichlorosilane
- PDMS:
-
Polydimethylsiloxane
- PET:
-
Polyethyleneterephthalate
- PPE:
-
Poly(phenylenethynylene)
- PPy:
-
Poly(pyrrole)
- PVC:
-
Polyvinylchloride
- QCM:
-
Quartz crystal microbalance
- RbSA:
-
Rabbit serum albumin
- SAM:
-
Self-assembled monolayer
- Try:
-
Tryptophan
- TSMR:
-
Thickness shear mode resonator
- Tym:
-
Tyrosinamide
- Tyr:
-
Tyrosine
References
Hembury GA, Borovkov VV, Inoue Y (2008) Chirality-sensing supramolecular systems. Chem Rev 108(1):1–73
Hutt AJ (2005) Drug chirality and its pharmacological consequences. In: Smith J (ed) Introduction to the principles of drug design and action. Harwood Academic, Amsterdam, pp 117–183
Ward TJ, Baker BA (2008) Chiral separations. Anal Chem 80:4363–4372
Garrison AW, Schmitt-Kopplin P, Avants JK (2008) Analysis of the enantiomers of chiral pesticides and other pollutants in environmental samples by capillary electrophoresis. In: Capillary electrophoresis, vol 384. Methods in molecular biology™. Humana, Totowa, pp 157–170
Zawirska-Wojtasiak R (2006) Chirality and the nature of food: authenticity of aroma. Acta Sci Pol Technol Aliment 5(1):21–36
Trojanowicz M, Kaniewska M (2008) Electrochemical chiral sensors and biosensors. Electroanalysis 21(3–5):229–238
Berthod A (2006) Chiral recognition mechanisms. Anal Chem 78(7):2093–2099
Cramer F (1994) The lock and key principle. Wiley, Chichester
Izake EL (2007) Chiral discrimination and enantioselective analysis of drugs: an overview. J Pharm Sci 96(7):1659–1676
Zhang J, Albelda MT, Liu Y, Canary JW (2005) Chiral nanotechnology. Chirality 17(7):404–420
Ali I, Saleem K, Hussain I, Gaitonde VD, Aboul-Enein HY (2009) Polysaccharides chiral stationary phases in liquid chromatography. Sep Purif Rev 38(2):97–147
Stefan-van Staden R-I, van Staden JF, Aboul-Enein HY, Mirica MC, Iorga M, Balcu I (2009) Maltodextrins as chiral selectors in biomedical enantioanalysis: a mini review. Open Chem Biomed Meth J 2:107–110
Shahgaldian P, Pieles U (2006) Cyclodextrin derivatives as chiral supramolecular receptors for enantioselective sensing. Sensors 6(6):593–615
Ohsawa K, Kasamatsu T, Nagashima J, Hanawa K, Kuwahara M, Ozaki H, Sawai H (2008) Arginine-modified DNA aptamers that show enantioselective recognition of the dicarboxylic acid moiety of glutamic acid. Anal Sci 24(1):167–172
Challier L, Mavre F, Moreau J, Fave C, Schollhorm B, Marchal D, Peyrin E, Noel V, Limoges B (2012) Simple and highly enantioselective electrochemical aptamer-based binding assay for trace detection of chiral compounds. Anal Chem 84(12):5415–5420
Maier NM, Lindner W (2007) Chiral recognition applications of molecularly imprinted polymers: a critical review. Anal Bioanal Chem 389(2):377–397
Yashima E, Maeda K, Nishimura T (2003) Detection and amplification of chirality by helical polymers. Chem-Eur J J10(1):42–51
Yashima E, Maeda K (2008) Chirality-responsive helical polymers. Macromolecules 41(1):3–12
Kane-Maguire LAP, Wallace GG (2010) Chiral conducting polymers. Chem Soc Rev 39(7):2545–2576
Badis M, Tomaszkiewicz I, Joly JP, Rogalska E (2004) Enantiomeric recognition of amino acids by amphiphilic crown ethers in Langmuir monolayers. Langmuir 20(15):6259–6267
Diamond D, Nolan K (2001) Peer reviewed: calixarenes: designer ligands for chemical sensors. Anal Chem 73(1):22–29
Guangyan Q, Shunying L, Yongbing H (2008) Chiral recognition based on calix[4]arene. Prog Chem 20(12):1933–1944
Pietraszkiewicz M, Prus P, Bilewicz R (1999) pH dependent enantioselection of amino acids by phosphorous-containing calix[4]resorcinarene in Langmuir monolayers. Polish J Chem 73:2035–2042
Wen W, Jingli H, Youzun C, Xiaojia H (2007) Progress in chiral sensors. Prog Chem 19(11):1820–1825
Maier NM, Franco P, Lindner W (2001) Separation of enantiomers: needs, challenges, perspectives. J Chromatogr A 906(1):3–33
Inagaki S, Min JZ, Toyo'oka T (2008) Prediction for the separation efficiency of a pair of enantiomers during chiral high-performance liquid chromatography using a quartz crystal microbalance. Anal Chem 80(5):1824–1828
Hierlemann A, Baltes H, Schurig V (2001) Search for extraterrestrial enantioenrichment by using chemical microsensors. Enantiomer 6(2–3):129
Trojanowicz M, Wcislo M (2005) Electrochemical and piezoelectric enantioselective sensors and biosensors. Anal Lett 38(4):523–547
Budnikov G, Evtyugin G, Budnikova YG, Al'fonsov V (2008) Chemically modified electrodes with amperometric response in enantioselective analysis. J Anal Chem 63(1):2–12
Stefan R-I, van Staden JF, Aboul-Enein HY (2004) Enantioselective, potentiometric membrane electrodes for the determination of l-pipecolic acid in serum. Electroanalysis 16(20):1730–1733
Stefan-van Staden R-I, Mashile TR (2006) Enantioselective assay of S(+)-ibuprofen using enantioselective, potentiometric membrane electrodes based on maltodextrins. Sens Actuators B 120(1):295–297
Stefan-van Staden R-I, Bokretsion RG, Ozoemena KI (2006) Utilization of maltodextrin-based enantioselective, potentiometric membrane electrodes for the enantioselective assay of S-flurbiprofen. Anal Lett 39(6):1065–1073
Ozoemena KI, Stefan R-I (2004) Enantioselective, potentiometric membrane electrodes based on maltodextrins: their applications for the determination of l-proline. Sens Actuators B 98(1):97–100
Stefan R-I, van Staden JKF, Aboul-Enein HY (2000) Simultaneous detection of S and R-captopril using sequential injection analysis. Talanta 51(5):969–975
Ozoemena KI, Stefan R-I, Staden JF, Aboul-Enein HY (2004) Utilization of maltodextrin based enantioselective, potentiometric membrane electrodes for the enantioselective assay of S-perindopril. Talanta 62(4):681–685
Stefan-van Staden R-I, Bokretsion RG, Ozoemena KI, van Staden JF, Aboul-Enein HY (2006) Enantioselective, potentiometric membrane electrodes based on different cyclodextrins as chiral selectors for the assay of S-flurbiprofen. Electroanalysis 18(17):1718–1721
Stefan R-I, van Staden JKF, Aboul-Enein HY (1999) Analysis of chiral drugs with enantioselective biosensors. An overview. Electroanalysis 11(16):1233–1235
Stefan R-I, van Staden JKF, Aboul-Enein HY (1999) A new construction for a potentiometric, enantioselective membrane electrode-its utilization to the S-captopril assay. Talanta 48(5):1139–1143
Aboul-Enein HY, Stefan R-I, van Staden JF (1999) Analysis of several angiotensin-converting enzyme inhibitors using potentiometric, enantioselective membrane electrodes. Anal Lett 32(4):623–632
Ratko AA, Stefan R-I, van Staden JKF, Aboul-Enein HY (2004) Enantioselective, potentiometric membrane electrode based on vancomycin: its application for the determination of d-pipecolic acid. Sens Actuators B 99(2):539–543
Ratko AA, Stefan R-I, van Staden JKF, Aboul-Enein HY (2004) Determination of l-carnitine using enantioselective, potentiometric membrane electrodes based on macrocyclic antibiotics. Talanta 63(3):515–519
Ratko AA, Stefan R-I, van Staden JKF, Aboul-Enein HY (2004) Macrocyclic antibiotics as chiral selectors in the design of enantioselective, potentiometric membrane electrodes for the determination of l- and d-enantiomers of methotrexate. Talanta 64(1):145–150
Stefan-van Staden R-I, Moldoveanu I, Sava D-F, Kapnissi-Christodoulou C, van Staden JF (2013) Enantioanalysis of pipecolic acid with stochastic and potentiometric microsensors. Chirality 25(2):114–118
Kaniewska M, Sikora T, Kataky R, Trojanowicz M (2008) Enantioselectivity of potentiometric sensors with application of different mechanisms of chiral discrimination. J Biochem Biophys Methods 70(6):1261–1267
Wulff G (1995) Molecular imprinting in cross-linked materials with the aid of molecular templates – a way towards artificial antibodies. Angew Chem Int Ed Engl 34(17):1812–1832
Andersson L, Sellergren BR, Mosbach K (1984) Imprinting of amino acid derivatives in macroporous polymers. Tetrahedron Lett 25(45):5211–5214
Chen Y, Chen L, Bi R, Xu L, Liu Y (2012) A potentiometric chiral sensor for l-phenylalanine based on crosslinked polymethylacrylic acid-polycarbazole hybrid molecularly imprinted polymer. Anal Chim Acta 754:83–90
Matsunaga M, Nakanishi T, Asahi T, Osaka T (2007) Highly enantioselective discrimination of amino acids using copper deposition on a gold electrode modified with homocysteine monolayer. Electrochem Commun 9(4):725–728
Zhou Y, Yu B, Levon K, Nagaoka T (2004) Enantioselective recognition of aspartic acids by chiral ligand exchange potentiometry. Electroanalysis 16(11):955–960
Davankov VA, Semechkin AV (1977) Ligand-exchange chromatography. J Chromatogr A 141(3):313–353
Galaverna G, Corradini R, Dallavalle F, Folesani G, Dossena A, Marchelli R (2001) Chiral separation of amino acids by copper(II) complexes of tetradentate diaminodiamido-type ligands added to the eluent in reversed-phase high-performance liquid chromatography: a ligand exchange mechanism. J Chromatogr A 922(1):151–163
Chen Z, Uchiyama K, Hobo T (2004) Chiral resolution of dansyl amino acids by ligand exchange-capillary electrophoresis using Cu(II)-l-prolinamides as chiral selector. Anal Chim Acta 523(1):1–7
Zhou Y, Nagaoka T, Yu B, Levon K (2009) Chiral ligand exchange potentiometric aspartic acid sensors with polysiloxane films containing a chiral ligand N-carbobenzoxy-aspartic acid. Anal Chem 81(5):1888–1892
Yang Y, Hou J, Li B, Xu L (2010) Enantioselective ITO electrode modified with chiral salen Co(II) complex. Chem Lett 39(7):690–691
Xu L, Yang Y, Wang Y, Gao J (2009) Chiral salen Mn (III) complex-based enantioselective potentiometric sensor for l-mandelic acid. Anal Chim Acta 653(2):217–221
Stoica AI, Vinas C, Teixidor F (2009) Cobaltabisdicarbollide anion receptor for enantiomer-selective membrane electrodes. Chem Commun 33:4988–4990
Matsunaga M, Ueno T, Nakanishi T, Osaka T (2008) Enantioselective potential response of a human serum albumin-modified ITO electrode for tryptophan. Electrochem Commun 10(12):1844–1846
Yin X, Ding J, Zhang S, Kong J (2006) Enantioselective sensing of chiral amino acids by potentiometric sensors based on optical active polyaniline films. Biosens Bioelectron 21(11):2184–2187
Lahav M, Kharitonov AB, Willner I (2001) Imprinting of chiral molecular recognition sites in thin TiO2 films associated with field-effect transistors: novel functionalized devices for chiroselective and chirospecific analyses. Chemistry 7(18):3992–3997
Matsunaga M, Yamamoto D, Nakanishi T, Osaka T (2010) Chiral discrimination between alanine enantiomers by field effect transistor with a homocysteine monolayer-modified gate. Electrochim Acta 55(15):4501–4505
Yamamoto D, Nakanishi T, Osaka T (2011) Chiral sensing system based on the formation of diastereomeric metal complex on a homocysteine monolayer using field effect transistor. Electrochim Acta 56(26):9652–9655
Chen Q, Zhou J, Han Q, Wang Y, Fu Y (2012) A new chiral electrochemical sensor for the enantioselective recognition of penicillamine enantiomers. J Solid State Electrochem 16:2481–2485
Fu Y, Wang L, Chen Q, Zhou J (2011) Enantioselective recognition of chiral mandelic acid in the presence of Zn (II) ions by l-cysteine-modified electrode. Sens Actuators B 155(1):140–144
Fu Y, Chen Q, Zhou J, Han Q, Wang Y (2012) Enantioselective recognition of mandelic acid based on γ-globulin modified glassy carbon electrode. Anal Biochem 421:103–107
Chen Q, Zhou J, Han Q, Wang Y, Fu Y (2012) The selective adsorption of human serum albumin on N-isobutyryl-cysteine enantiomers modified chiral surfaces. Biochem Eng J 69:155–158
Basozabal I, Gomez-Caballero A, Unceta N, Goicolea MA, Barrio RJ (2011) Voltammetric sensors with chiral recognition capability: the use of a chiral inducing agent in polyaniline electrochemical synthesis for the specific recognition of the enantiomers of the pesticide dinoseb. Electrochim Acta 58:729–735
Huang J, Wei Z, Chen J (2008) Molecular imprinted polypyrrole nanowires for chiral amino acid recognition. Sens Actuators B 134(2):573–578
Prasad BB, Madhuri R, Tiwari MP, Sharma PS (2010) Enantioselective recognition of d- and l-tryptophan by imprinted polymer-carbon composite fiber sensor. Talanta 81(1):187–196
Prasad BB, Tiwari MP, Madhuri R, Sharma PS (2011) Enantioselective separation and electrochemical sensing of d- and l-tryptophan at ultratrace level using molecularly imprinted micro-solid phase extraction fiber coupled with complementary molecularly imprinted polymer-fiber sensor. J Chromatogr B 879(5):364–370
Stefan R-I, van Staden JKF, Aboul-Enein HY (2000) Amperometric biosensors/sequential injection analysis system for simultaneous determination of S- and R-captopril. Biosens Bioelectron 15(1):1–5
Stefan R-I, van Staden JF, Aboul-Enein HY (2003) Biosensors for the enantioselective analysis of pipecolic acid. Sens Actuators B 94(3):271–275
Stefan R-I, Bokretsion RG, van Staden JF, Aboul-Enein HY (2003) Determination of l- and d-enantiomers of methotrexate using amperometric biosensors. Talanta 60(5):983–990
Stefan-van Staden R-I, van Staden JF, Aboul-Enein HY (2012) Amperometric biosensor based on diamond paste for the enantioanalysis of l-lysine. Biosens Bioelectron 35:439–442
Granot E, Tel-Vered R, Lioubashevski O, Willner I (2008) Stereoselective and enantioselective electrochemical sensing of monosaccharides using imprinted boronic acid-functionalized polyphenol films. Adv Funct Mater 18(3):478–484
Ide J, Nakamoto T, Moriizumi T (1995) Discrimination of aromatic optical isomers using quartz-resonator sensors. Sens Actuators A 49(1):73–78
Bodenhöfer K, Hierlemann A, Juza M, Schurig V, Göpel W (1997) Chiral discrimination of inhalation anesthetics and methyl propionates by thickness shear mode resonators: new insights into the mechanisms of enantioselectivity by cyclodextrins. Anal Chem 69(19):4017–4031
Fietzek C, Hermle T, Rosenstiel W, Schurig V (2001) Chiral discrimination of limonene by use of β-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks. Fresenius J Anal Chem 371(1):58–63
Kieser B, Fietzek C, Schmidt R, Belge G, Weimar U, Schurig V, Gauglitz G (2002) Use of a modified cyclodextrin host for the enantioselective detection of a halogenated diether as chiral guest via optical and electrical transducers. Anal Chem 74(13):3005–3012
Ng SC, Sun T, Chan HSO (2003) Durable chiral sensor based on quartz crystal microbalance using self-assembled monolayer of permethylated β-cyclodextrin. Macromol Symp 192:171–182
Ng SC, Sun T, Chan HSO (2002) Chiral discrimination of enantiomers with a self-assembled monolayer of functionalized β-cyclodextrins on Au surfaces. Tetrahedron Lett 43(15):2863–2866
Xu C, Ng SC, Chan HSO (2008) Self-assembly of perfunctionalized β-cyclodextrins on a quartz crystal microbalance for real-time chiral recognition. Langmuir 24(16):9118–9124
Luo ML, Zhang WG, Zhang S, Fan J, Su WC, Yin X (2010) Self-assembly and chiral recognition of quartz crystal microbalance chiral sensor. Chirality 22(4):411–415
Haupt K, Noworyta K, Kutner W (1999) Imprinted polymer-based enantioselective acoustic sensor using a quartz crystal microbalance. Anal Commun 36(11–12):391–393
Piacham T, Josell A, Arwin H, Prachayasittikul V, Ye L (2005) Molecularly imprinted polymer thin films on quartz crystal microbalance using a surface bound photo-radical initiator. Anal Chim Acta 536(1):191–196
Percival C, Stanley S, Galle M, Braithwaite A, Newton M, McHale G, Hayes W (2001) Molecular-imprinted, polymer-coated quartz crystal microbalances for the detection of terpenes. Anal Chem 73(17):4225–4228
Stanley S, Percival C, Morel T, Braithwaite A, Newton M, McHale G, Hayes W (2003) Enantioselective detection of l-serine. Sens Actuators B 89(1):103–106
Cao L, Zhou XC, Li SFY (2001) Enantioselective sensor based on microgravimetric quartz crystal microbalance with molecularly imprinted polymer film. Analyst 126(2):184–188
Liu F, Liu X, Ng SC, Chan HSO (2006) Enantioselective molecular imprinting polymer coated QCM for the recognition of l-tryptophan. Sens Actuators B 113(1):234–240
Syritski V, Reut J, Menaker A, Gyurcsanyi RE, Opik A (2008) Electrosynthesized molecularly imprinted polypyrrole films for enantioselective recognition of l-aspartic acid. Electrochim Acta 53(6):2729–2736
Kong Y, Zhao W, Yao S, Xu J, Wang W, Chen Z (2010) Molecularly imprinted polypyrrole prepared by electrodeposition for the selective recognition of tryptophan enantiomers. J Appl Polym Sci 115(4):1952–1957
Huang J, Egan VM, Guo H, Yoon JY, Briseno AL, Rauda IE, Garrell RL, Knobler C, Zhou F, Kaner RB (2003) Enantioselective discrimination of d- and l-phenylalanine by chiral polyaniline thin films. Adv Mater 15(14):1158–1161
Tanese M, Torsi L, Cioffi N, Zotti L, Colangiuli D, Farinola G, Babudri F, Naso F, Giangregorio M, Sabbatini L (2004) Poly(phenyleneethynylene) polymers bearing glucose substituents as promising active layers in enantioselective chemiresistors. Sens Actuators B 100(1):17–21
Guo HS, Kim JM, Chang SM, Kim WS (2009) Chiral recognition of mandelic acid by l-phenylalanine-modified sensor using quartz crystal microbalance. Biosens Bioelectron 24(9):2931–2934
Guo HS, Kim JM, Kim SJ, Chang SM, Kim WS (2009) Versatile method for chiral recognition by the quartz crystal microbalance: chiral mandelic acid as the detection model. Langmuir 25(2):648–652
Kim JM, Chang SM, He XK, Kim WS (2012) Development of real-time sensitive chiral analysis technique using quartz crystal analyzer. Sens Actuators B 171–172:478–485
Landsteiner K, Van der Scheer J (1928) Serological differentiation of steric isomers. J Exp Med 48(3):315–320
Dutta P, Tipple C, Lavrik N, Datskos P, Hofstetter H, Hofstetter O, Sepaniak M (2003) Enantioselective sensors based on antibody-mediated nanomechanics. Anal Chem 75(10):2342–2348
Su WC, Zhang WG, Zhang S, Fan J, Yin X, Luo ML, Ng SC (2009) A novel strategy for rapid real-time chiral discrimination of enantiomers using serum albumin functionalized QCM biosensor. Biosens Bioelectron 25(2):488–492
Chen WJ, Zhang S, Zhang WG, Fan J, Yin X, Zheng SR, Su WC, Zhang Z, Hong T (2012) A new biosensor for chiral recognition using goat and rabbit serum albumin self-assembled quartz crystal microbalance. Chirality 24:804–809
Nakanishi T, Yamakawa N, Asahi T, Shibata N, Ohtani B, Osaka T (2004) Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality. Chirality 16(S1):S36–S39
Guo W, Wang J, Wang C, He J-Q, X-W H, Cheng J-P (2002) Design, synthesis, and enantiomeric recognition of dicyclodipeptide-bearing calix[4]arenes: a promising family for chiral gas sensor coatings. Tetrahedron Lett 43(32):5665–5667
Severin EJ, Sanner RD, Doleman BJ, Lewis NS (1998) Differential detection of enantiomeric gaseous analytes using carbon black-chiral polymer composite, chemically sensitive resistors. Anal Chem 70(7):1440–1443
Costello BPJ, Ratcliffe NM, Sivanand PS (2003) The synthesis of novel 3-substituted pyrrole monomers possessing chiral side groups: a study of their chemical polymerisation and the assessment of their chiral discrimination properties. Synth Met 139(1):43–55
Torsi L, Marinelli F, Angione MD, Dell'Aquila A, Cioffi N, Giglio ED, Sabbatini L (2009) Contact effects in organic thin-film transistor sensors. Org Electron 10(2):233–239
Torsi L, Dodabalapur A (2005) Organic thin-film transistors as plastic analytical sensors. Anal Chem 77(19):380–387
Torsi L, Dodabalapur A, Sabbatini L, Zambonin PG (2000) Multi-parameter gas sensors based on organic thin-film-transistors. Sens Actuators B 67(3):312–316
Torsi L, Tafuri A, Cioffi N, Gallazzi M, Sassella A, Sabbatini L, Zambonin P (2003) Regioregular polythiophene field-effect transistors employed as chemical sensors. Sens Actuators B 93(1):257–262
Majewski LA, Schroeder R, Grell M (2005) One volt organic transistor. Adv Mater 17(2):192–196
Dost R, Das A, Grell M (2007) A novel characterization scheme for organic field-effect transistors. J Phys D Appl Phys 40(12):3563
Roberts ME, Mannsfeld SCB, Queralto N, Reese C, Locklin J, Knoll W, Bao Z (2008) Water-stable organic transistors and their application in chemical and biological sensors. Proc Natl Acad Sci 105(34):12134–12139
Sokolov AN, Roberts ME, Bao Z (2009) Fabrication of low-cost electronic biosensors. Mater Today 12(9):12–20
Angione MD, Cotrone S, Magliulo M, Mallardi A, Altamura D, Giannini C, Cioffi N, Sabbatini L, Fratini E, Baglioni P (2012) Interfacial electronic effects in functional biolayers integrated into organic field-effect transistors. Proc Natl Acad Sci 109(17):6429–6434
Torsi L, Farinola GM, Marinelli F, Tanese MC, Omar OH, Valli L, Babudri F, Palmisano F, Zambonin PG, Naso F (2008) A sensitivity-enhanced field-effect chiral sensor. Nat Mater 7(5):412–417
Bernards DA, Macaya DJ, Nikolou M, DeFranco JA, Takamatsu S, Malliaras GG (2007) Enzymatic sensing with organic electrochemical transistors. J Mater Chem 18(1):116–120
Ouyang R, Lei J, Ju H, Xue Y (2007) A molecularly imprinted copolymer designed for enantioselective recognition of glutamic acid. Adv Funct Mater 17(16):3223–3230
Zhang S, Ding J, Liu Y, Kong J, Hofstetter O (2006) Development of a highly enantioselective capacitive immunosensor for the detection of α-amino acids. Anal Chem 78(21):7592–7596
Kurzawski P, Bogdanski A, Schurig V, Wimmer R, Hierlemann A (2007) Opposite signs of capacitive microsensor signals upon exposure to the enantiomers of methyl propionate compounds. Angew Chem Int Ed 47(5):913–916
Kurzawski P, Bogdanski A, Schurig V, Wimmer R, Hierlemann A (2009) Direct determination of the enantiomeric purity or enantiomeric composition of methylpropionates using a single capacitive microsensor. Anal Chem 81(5):1969–1975
Kurzawski P, Schurig V, Hierlemann A (2009) Chiral sensing using a complementary metal-oxide semiconductor-integrated three-transducer microsensor system. Anal Chem 81(22):9353–9364
Hofstetter O, Hofstetter H, Wilchek M, Schurig V, Green BS (1999) Chiral discrimination using an immunosensor. Nat Biotechnol 17(4):371–374
Shahgaldian P, Hegner M, Pieles U (2005) A cyclodextrin self-assembled monolayer (SAM) based surface plasmon resonance (SPR) sensor for enantioselective analysis of thyroxine. J Incl Phenom Macrocycl Chem 53(1):35–39
Lieberman I, Shemer G, Fried T, Kosower EM, Markovich G (2008) Plasmon-resonance-enhanced absorption and circular dichroism. Angew Chem Int Ed 47(26):4855–4857
Ha JM, Solovyov A, Katz A (2008) Postsynthetic modification of gold nanoparticles with calix[4]arene enantiomers: origin of chiral surface plasmon resonance. Langmuir 25(1):153–158
Ha JM, Solovyov A, Katz A (2009) Synthesis and characterization of accessible metal surfaces in calixarene-bound gold nanoparticles. Langmuir 25(18):10548–10553
Ben-Amram Y, Riskin M, Willner I (2010) Selective and enantioselective analysis of mono- and disaccharides using surface plasmon resonance spectroscopy and imprinted boronic acid-functionalized Au nanoparticle composites. Analyst 135(11):2952–2959
Bodenhöfer K, Hierlemann A, Seemann J, Gauglitz G, Christian B, Koppenhoefer B, Göpel W (1997) Chiral discrimination in the gas phase using different transducers: thickness shear mode resonators and reflectometric interference spectroscopy. Anal Chem 69(15):3058–3068
Bodenhöfer K, Hierlemann A, Seemann J, Gauglitz G, Koppenhoefer B, Göpel W (1997) Chiral discrimination using piezoelectric and optical gas sensors. Nature 387:577–579
Nopper D, Lammershop O, Wulff G, Gauglitz G (2003) Amidine-based molecularly imprinted polymers-new sensitive elements for chiral chemosensors. Anal Bioanal Chem 377(4):608–613
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Manoli, K., Magliulo, M., Torsi, L. (2013). Chiral Sensor Devices for Differentiation of Enantiomers. In: Schurig, V. (eds) Differentiation of Enantiomers II. Topics in Current Chemistry, vol 341. Springer, Cham. https://doi.org/10.1007/128_2013_444
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DOI: https://doi.org/10.1007/128_2013_444
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