摘要
本论文基于荧光传感器PET(光诱导电子转移)机理,利用对甲基苯硼酸、1-萘甲醛、8-羟基喹啉等原料,合成了两种有机化合物:化合物1-[ N -(2-phosphoryl)- N -(boronobenzyl)] benzyl naphthalene(简称:NPBBN)和化合物N-(boronobenzyl)-8-hydroxyquinolinium bromide(简称:BHQB),并分别对其性能进行了一系列测试。
对于化合物NPBBN体系,我们先考查了不同pH值对其荧光变化的影响,由此我们选取了pH= 6.86的缓冲溶液对几种不同的单糖分子进行了检测,在相同条件下化合物NPBBN对单糖的识别能力是不同的。此外,我们引入了CTAB(十六烷基三甲基溴化铵)阳离子表面活性剂,来提高该传感器体系的灵敏度。
对于化合物BHQB体系,我们先对其与单糖识别进行了荧光测试,归属了两个发射峰分别对应的化合物BHQB的不同状态。还对该体系与单糖识别后的紫外可见光谱进行了研究,证明了该体系作为糖荧光传感器的可行性。
总之,我们设计合成了两种含硼酸和不同荧光发色团的有机化合物,并分别对其性能进行了研究,该体系可以作为新型的糖荧光传感器,用于体外及体内检测。
Saccharides play a critical role in a variety of biological processes, such as offering energy for human bodies, which can be found easily in nature. Meanwhile, saccharides recognition and detection are very important in medical area, cell-biology and food industry. Developing chemosensor for saccharides recognition selectively attracts a lot of chemistry workers. Sugar sensors commonly consist of receptor, linker and reporter. Recent years, boronic acid compounds are widely used for saccharides recognition, because boronic acids can readily and reversibly form cyclic boronate esters with 1,2- or 1,3- hydroxy groups of saccharides via two covalent bonds to switch a photoelectron transfer process , which largely changed the fluorescence intensity of chromophore. So, boronic acid-based fluorescent chemosensors are widely developed.
Based on the mechanism of PET ( photoinduced electron transfer ), we synthesized two boronic acid compounds using p-tolylboronic acid, 8-Hydroxyquinoline, 1-Naphthaldehyde and so on. One is 1-[ N -(2-phosphoryl)- N -(boronobenzyl)] benzyl naphthalene(NPBBN), the other is N-(boronobenzyl)-8-hydroxyquinolinium bromide ( BHQB ) , these two compounds are both water soluble. We also detected their properties respectively, in order to construct novel and effective sugar sensors.
Compound NPBBN contains boronic acid as the receptor and naphthalene as the reporter. At the beginning, we studied the relationship between the fluorescence intensity and the pH value of the aqueous solution. Firstly, we prepared compound NPBBN solution (1×10-4M) buffered at different pH values and D-fructose solution (1M). Compared with the NPBBN system without D-fructose, in the range of near physiological pH values, the fluorescence intensity of that in the presence of D-fructose changed a lot. It’s because the boronic acid in receptor formed a stable five-membered cyclic boronate ester with the saccharide , which resulted in the electronic cloud density of fluorophore decreased. Therefore, the fluorescence intensity was increased obviously. According to experiment above, we chose pH=6.86 as the proper condition to further the following detection. Then we tested the recognition of compound NPBBN for different saccharides. We prepared the NPBBN aqueous solution (1×10-4M) with pH=6.86 buffer, and we chose three different sugar containing diol structure. From the test we found that, in the same circumstance, compound NPBBN system has various recognition abilities for these saccharides. The selective order is D-fructose(Ka=207) > D-galactose(Ka=41)> D-glucose( Ka=11 ) ,which demonstrated that this system tend to combine with fructofuranose rather than galactopyranose and glucopyranose . Therefore the NPBBN compound system we designed can be applied to sugar recognition for different monosaccharides selectively. Furthermore, we introduced CTAB (cetyltrimethyammonium bromide), which is a kind of cation surfactant , with the aim to improve the response of single NPBBN system .Compared the two systems that is in the absence and presence of CTAB , we discovered that the fluorescence intensity of the mixed aqueous solution system with NPBBN and CTAB remarkably increased. The reason of this change is that CTAB can be self-organized to micelle in aqueous solution, the hydrophilic head groups bearing positive charge attracted the phosphate radicals bearing negative charge of compound NPBBN. Then a lot of NPBBN molecular aggregated on the micelle surface, in other words, the local concentration of compound NPBBN was enhanced. So, the fluorescence intensity depending on the fluorophore concentration of this mixed system was obviously increased.
Compound BHQB contains boronic acid as the receptor and 8-Hydroxyquinoline as the reporter. We still chose pH=6.86 buffer to prepare the samples in our experiments. We prepared BHQB aqueous solution (1×10-4M) and D-fructose (1M) solution. At first we examined the excitation wave and emission wave, according to the fluorescence spectra, we can see that the excitation wavelength of BHQB is about 372nm, and meanwhile there are two emission wavelengths about 430nm and 520nm. This might show that there are two states of compound BHQB in solution. One is free boronic acid containing the B which is sp2 hybridigation, the other is boronic acid containing the B which is sp3 hybridigation due to combination with hydroxyl groups in aqueous solution. They are in equilibrium state and can be transformed into each other. In order to figure out the corresponding state of the two emission wavelengths, we checked the emission spectra and absorption spectra of BHQB system adding D-fructose and the result is conformable. The boronic acid receptor of compound BHQB binding with the hydroxy of D-fructose formed boronate esters, which induced the elector from quinolinium ring transfer to B atom. So the fluorescence was quenched resulting in the enhancement of fluorescence intensity, which was reflected by the increase of 430nm emission wavelength. The formation of boronate esters lowered the concentration of free boronic acid and broke the equilibrium. The boronic acid with B of sp3 hybridigation transformed into free boronic acid with B of sp2 hybridigation , which was reflected by the decrease of 510nm emission wavelength.
In conclusion, there are two compounds containing boronic acid and different fluorophores were synthetized and their properties were studied. Compounds NPBBN and BHQB are both water soluble, gives signals adding mono saccharides in the near physiological pH buffer solution. All these merits make them ideal sugar sensors for detection in vitro and in vivo.
引文
[1]SUBRAHMANYAM S, PILETSKY S A, PILETSKA E V, et al.‘Bite-and-Switch’approach using computationally designed molecularly imprinted polymers for sensing of creatinine [J]. Biosensors and Bioelectronics,2001,16(9-12):631-637.
[2]CZARNIK A W. Chemical Communication in Water Using Fluorescent Chemosensors [J]. Acc. Chem. Res,1994,27(10):302-308.
[3]陈中举,张燕玲,黄金瑛.国外医学生物医学工程分册[M].2004, 27(6): 348-3521
[4]LV ZZ, ZHANG YY. Synthesis of BODIPY-FL-labeled Phenylephrine and the Determination of Its Biological Activity [J].Peking Univ (Health Sciences),2004,36(6):623-625
[5]范雯.国外医学药学分册[M].2007,( 34) : 52-55
[6]吴世康.超分子光化学导论-基础与应用[M].科学出版社, 2005.
[7]JAMES T D, SANDANAYAKE K R A S, SHINKAI S. Fluorscent sensor compounds for detecting saccharides [J].Nature(London),1995,374,345
[8]DICESARE N, LAKOWICZ J R. Chalcone-analogue fluorescent probes for saccharides signaling using the boronic acid group [J].Tetrahedron lett.,2002,43:2615-2618
[9]GAO X, ZHANG Y, WANG B A. New Boronic Acid Fluorescent Reporter Compounds II. A Naphthalene-based Sensor Functional at Physiological pH. [J].Org. Lett.,2003,5:4615-4618
[10]DICESARE N, LAKOWICZ J R. Spectral Properties of Fluorophores Combining the Boronic Acid Group with Electron Donor or Withdrawing Groups. Implication in the Development of Fluorescence Probes for Saccharides [J].Phys. Chem. A, 2001,105: 6834-6840
[11]GRABOWSKI Z R, ROTKIEWICZ K, SIEMIARCZUK A, et al. Twisted Intramolecular Charge Transfer States (TICT). A New Class of Excited States with a FullCharge Separation [J].Nouv Chim,1979,3:443
[12]ZACHARIASSE K A, GROBYE M, VONDER HAART, et al . Intramolecular charge transfer in the excited state. Kinetics and configurational changes [J].Photochem Photobiol A : Chem,1996,102:59-70
[13]SOBOLEWSKI A L, DOMCKE W. Promotion of intramolecular charge transfer in dimethylamino derivatives: twisting versus acceptor-group rehybridization [J].Chem Phys Lett.,1996, 259:119
[14] SOBOLEWSKI A L,DOMCKE W. Charge transfer in aminobenzonitriles: do they twist? [J].Chem Phys Lett.,1996,250:428
[15]江云宝.分子内电荷转移双重荧光传感与分子识别[J].福州大学学报(自然科学版),1999(S1):11-12
[16]REDDY L RAJENDER, REDDY M ARJYUN, BHANUMATHI N, RAO K RAMA. A new fluorescent chemosensor: synthesis and molecular recognition by sulfamidopyrrolidinylidene modifiedβ-cyclodextrin [J]. Chem. Res, 2000, Vol.2000, No.10 :494-495
[17]J L YANG, H Z LIN, M ZHENG, F L BAI. Fluorescence Spectra of Model Compounds for Light-emitting Alternating Copolymers in Heterogeneous Environments [J]. Chinese Chemical Letters, 2001,Vol.12, No.4, 369-372,
[18]JIANG Y B, JIN M G, LIN L R, et al. Spectroscopic characterization of intramolecular charge ransfer of sodium 4-(N,N-dimethylamino)naphthalene-1-sulfonate [J]. Spectrochim Acta Part A: Molecular and Biomolecular Spectroscopy, 2004, Vol. 60, No.10 , 2209-2213
[19]JIANG Y B, JIN M G. Intramolecular charge transfer at reverse micelle–water pool interface: p-N,N-dimethylaminobenzoic acid in AOT/cyclohexane/water reverse micelle [J].Spectrochim Acta, Part A, 2000, Vol.56, No. 4 , 623-627
[20]H TAKAHASHIA, S TSUBOYAMAA, Y UMEZAWAB, K HONDAC, M NISHIO. CH/πInteractions as Demonstrated in the Crystal Structure of Host/Guest Compounds. ADatabase Study [J]. Tetrahedron , 2000, Vol.56, No.34 , 6185-6191
[21]COOPER C R, JAMES T D. Selective fluorescence signalling of saccharides in their furanose form [J]. Chem. Lett, 1998,9:883-884
[22]刘育,等.超分子化学——合成受体的分子识别与组装[M].天津:南开大学出版社,2001.
[23]SATO M, et al. Fluorescent chemo-sensor for organic guests based on regioselectively modified 6A,6B-, 6A,6C-, and 6A,6D-bis-dansylglycinemodified-Cyclodextrins [J].Anal.Sci,1999,15:1199-1205
[24]UCNO A. Review: Fluorescent cyclodextrins for molecule sensing [J].Supramol.Sci,1996,3:31-36
[25]PAGLIARI S, et al. Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescentβ-cyclodextrins [J].Tetrahedron Lett.,2000,41:3691-3695
[26]吕鉴泉,等.杯芳烃的功能化修饰及其在分子识别中的应用[J].化学进展, 2001,13: 209-215
[27]丁立平,高莉宁,房喻.基于主客体作用的荧光传感器研究进展[J].科技进展, Ziran Zazhi Vol.25, No.5
[28]许胜,刘斌,田禾.阴离子荧光化学传感器新进展[J].PROGRESS IN CHEMISTRY, 2006, Vol.18, No.6
[29]Y K Wu, X J Peng, J L Fan, S Gao, M Z Tian, J Z Zhao, S G Sun. Fluorescence Sensing of Anions Based on Inhibition of Excited-State Intramolecular Proton Transfer [J]. Org. Chem. 2007, 72, 62-70
[30]XINGMING GAO, YANLING ZHANG , BINGHE WANG. A highly fluorescent water-soluble boronic acid reporter for saccharide sensing that shows ratiometric UV changes and significant fluorescence changes [J].Tetrahedron, 2005,61: 9111-9117
[31]ERK C. Cation recognition with fluorophore crown ethers [J]. Ind.Eng.Chem. Res,2000,39: 3582-3588
[32]PRODI L, et al.An effective fluorescent chemosensor for mercury ions [J]. Am. Chem. Soc,2000,122: 6769-6770
[33]CORRADINI R, et al. A modified cyclodextrin with a fully encapsulateddansyl group: self-inclusion in the solid state and in solution [J].Chem.Eur,1996,2:373-381
[34] CORRADINI R, et al. Fluorescent chemosensor for organic guests and copper(II) ion based on dansyldiethyl enetriamine-modifiedβ-cyclodextrin [J].Org. Chem,1997,62:6283-6289
[35]HAMADA F, et al. Fluorescent sensors for molecules. Guest-responsive monomer and excimer fluorescence of 6A,6B-; 6A,6C-; 6A,6D-; and 6A,6E-bis(2-naphthylsulfonyl)-γ–cyclodextrins [J].Bull. Chem. Soc.Jpn, 1997,70:1339-1346
[36]NARITA M, HAMADA F.The synthesis of a fluorescent chemo-sensor system based on regioselectively dansyl-tosyl-modifiedβ- andγ-cyclodextrins [J]. Chem. Soc, Perkin Trans,2,2000,(2): 823-832
[37]解宏智,等.以二甲氨基查尔酮修饰的β-环糊精衍生物的合成及其分子识别作用的研究[J].自然科学进展,1999,9:1220-1227
[38]HOSSAIN M A, et al. Guest-induced diminishment in fluorescence quenching and molecule sensing ability of a novel cyclodextrin-peptide conjugate [J]. Am. Chem. Soc,2001,123:7435-7436
[39]WENQIAN YANG, JUN YAN, GREG SPRINGSTEEN, SUSAN DEETER, BINGHE WANG. A Novel Type of Fluorescent Boronic Acid That Shows Large Fluorescence Intensity Changes Upon Binding with a Carbohydrate in Aqueous Solution at Physiological Ph [J]. Bioorganic & Medicinal Chemistry Letters,2003,13:1019-1022
[40]WENQIAN YANG, A LI LINA, BINGHE WANG. a new type of boronic acid fluorescent reporter compound for sugar recognition [J]. Tetrahedron Letters,2005, 46:7981-7984
[41]沈燕清.利用荧光探针研究水溶性高分子溶液的结构[J].感光科学与光化学,1996,14:261-265
[42]KUHN H, et al. Frank-Kamenetskii, Hybridization of DNA and PNA molecularbeacons to single-stranded and double-stranded DNA targets [J]. Am. Chem. Soc., 2002,124: 1097-1103
[43]ARIMORI S, et al. A modular fluorescence intramolecular energy transfer saccharide sensor [J].Org. Lett., 2002,4: 4249-4251
[44]JEONG K S, et al. Convergent functional groups. 10. Molecular recognition of neutral substrates [J]. Am. Chem. Soc., 1991,113: 201-209
[45]张树政,等.糖生物学与糖生物工程[M].清华大学出版社, 2002.
[46]吴东儒,等.糖类生物化学[M].高等教育出版社, 1987.
[47][英]莫琳·E·泰勒、库尔特·德里卡默.糖生物学导论[M].化学工业出版社,2006.
[48]柳清湘,徐凤波,李庆山,曾宪顺,张正之.硼酸及其衍生物在荧光分子开关中的应用[J].化学通报,2002,Vol.65,No.10
[49]MARK J MANNIS. The use of antimicrobial peptides in ophthalmology: an experimental study in corneal preservation and the management of bacterial keratitis [J]. Trans Am Ophthalmol Soc, 2002, 100 : 243–271
[50]LINDBERG S E, WALLSCHLAGER D, PRESTBO F M, et al. Methylated mercury species in municipal waste landfill gas sampled in Florida [J]. USA Atmospheric Environment, 2001, 35(23): 4011-4015.
[51]张希,等.超分子化学[M].吉林大学出版社, 1995.
[52]孙向英,荧光传感受体分子的设计、组装与分子识别[D].厦门:厦门大学, 2003.
[53]DAVIS A P, WAREHEM R S. Carbohydrate Recognition through Noncovalent Interactions: A Challenge for Biomimetic and Supramolecular Chemistry [J]. Angew.Chem. Int. Ed., 1999, 38: 2978-2996.
[54]JAMES J H, JAMES T D. Synthetic receptors [J]. Chem. Soc. Perkin Trans.,2000,1:3155-3184.
[55]RUSIN O, KRAL V. Novel macrocycles with 1,1’-binaphthyl substituents for the recognition of saccharides [J]. Chem. Commun.,1999,2367-2368
[56]KRAL V, RUSIN O. Porphyrin phosphonates: novel anionic receptors for saccharide recognition [J]. Tetrahedron Lett., 2000, 41: 10147-10151.
[57]CHARVATOVA J, RUSIN O, KRAL. Novel porphyrin based receptors for saccharide recognition in water [J]. Sensors and Actuators B, 2001, 76: 366-372.
[58]RYAN T J, GREGORY L. TRINIDAD V, ANTHONY P. Davis Phase transfer of monosaccharides through noncovalent interactions: Selective extraction of glucose by a lipophilic cage receptor [J]. Proc Natl Acad Sci U S A.,2002,16,99(8): 4863–4866.
[59]ARIMORI S, BOSCH L I, WARD C. Fluorescent internal charge transfer (ICT) saccharide sensor [J].Tetrahedron Lett., 2001, 42: 4553-4555.
[60]DE JONGE N, LAMYL Y, SCHOOTS K, OOSTERKAMP T. H. High brightness electron beam from a multiwalled carbon nanotube [J].Nature 420, 393–395 (2002).
[61]RUSIN O, LANG K, KRAL V. Multivalent Cyclooligosaccharides: Versatile Carbohydrate Clusters with Dual Role as Molecular Receptors and Lectin Ligands [J]. Chem. Eur. 2002, 8: 655.
[62]XINGMING GAO, YANLING ZHANG, BINGHE WANG. Naphthalene-based water-soluble fluorescent boronic acid isomers suitable for ratiometric and off-on sensing of saccharides at physiological PH [J].New J.Chem,2005,29,579-586
[63]SCHUHMANN W, SCHMIDT H L. Poly(3,4-ethylenedioxythiophene)-Based Glucose Biosensors [J]. Adv. Biosensors, 1992, 2: 79.
[64]NAGY L, NAGY G, HAJOS P. Copper electrode based amperometric detector cell for sugar and organic acid measurements [J]. Sensors and Actuators B: Chemical , 2001, 76: 494-499.
[65]TAKEUCHI M, MIZUNO T, SHINKAI S. Asymmetric synthesis ofα-amino acidsusing polymer-supported Cinchona alkaloid-derived ammonium salts as chiral phase-transfer catalysts [J]. Tetrahedron: Asymmetry ,2000, Vol. 11, (16 ): 3277-3281
[66]STEFAN FRANZEN, WEIJUAN NI, BINGHE WANG. Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design [J]. Phys.Chem.B, 2003,107.12942-12948
[67]NAGAI Y, MKABAYASHI K, TOI H, et al . Stabilization of Sugar-Boronic Esters of Indolylboronic Acid in Water via Sugar–Indole Interaction: A Notable Selectivity in Oligosaccharides [J]. Bull . Chem. Soc. Jpn. ,1993 ,66(10) :2965-2971.
[68]RAJEEV S, JEREMY P C, JAMES A H MURRAY. Parameters affecting lithium acetate-mediated transformation of Saccharomyces cerevisiae and development of a rapid and simplified procedure [J]. Curr Genet, 1993,24:455-459
[69] BISSEL T AM DE SILVA A P. Gunaratna H Q M. Molecular fluorescent signalling with‘fluor–spacer–receptor’systems: approaches to sensing and switching devices via supramolecular photophysics [J].Chem. Soc. Rev, 1992 ,21 (3) :187-195.
[70]JAMES T D, SANDANAYAKE K R A S, SHHINKAI S. Novel photoinduced electron-transfer sensor for saccharides based on the interaction of boronic acid and amine [J]. Chem. Soc. ,Chem. Commun, 1994,477-478.
[71]REBEK J. Determining the functional conformations of biologically active peptides. [J]. Acc. Chem. Res. ,1990 ,23 (10) :338-344.
[72]NORRILD J C, EGGERT H . Molecular Recognition and Membrane Transport with Mixed-Ligand Borates [J]. Am. Chem. Soc, 1995 ,117 (5) :1479-1484.
[73]JAMES T D, SHINKAI S. N,N'-Bis(3-pyridiniomethyl)-4,4'-benzidinediium tetrachloride dihydrate [J]. Chem. Lett , 1996,503-504.
[74]J SCHATZ, F SCHILDBACH, A LENTZ, S RASTATTER. Thermal gravimetry, mass spectrometry and solid-state 13C NMR spectroscopy—simple and efficient methods to characterize the inclusion behaviour of p-tert-butylcalix[n]arenas [J]. Chem. Soc.,Perkin Trans. 2, 1998, 75 - 78
[75]GUTSCHE C D. Calixarenes[M].Cambridge and London :Roysl Society of Chemistry 1989 ,1 :223.
[76]WANG W, SPRINGSTEEN G, GAO S, et al . The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations [J]. Chem. Commun. ,2000 ,1283.
[77]GURPREET KAUR, HAO FANG, XINGMING GAO, HAIBO LI, BINGHE WANG.Substituent effct on anthracene-based bisboronic acid glucose sensors [J].Tetrahedron,2006,62:2583-2589
[78]CHRISTOPHER R COOPER, TONY D JAMES.Synthesis and evaluation of D-glucosamine-selective fluorescent sensors [J].Chem. Soc., Perkin Trans. 1,2002,963-969
[79]WILEY J P, HUGHES K A, KAISER R J, KESICKI E A, LUND K P, STOLOWITZ M L. Phenylboronic Acid?Salicylhydroxamic Acid Bioconjugates. 2. Polyvalent Immobilization of Protein Ligands for Affinity Chromatography [J].Bioconjugate Chem,2001,12, 240-250.
[80]DARDINER S J, SMITH B D, DUGGAN P J, KARPA M J, GRIFFIN G J. Selective Fructose Transport Through Supported Liquid Membranes Containing Diboronic Acid or Conjugated Monoboronic Acid-Quaternary Ammonium Carriers [J].Tetrahedron,1999, 55, 2857-2864.
[81]SUSUMU ARIMORI, MICHAEL L BELL, CHAN S OH, KARINE A FRIMAT, JAMES T D. Modular fluorescence sensors for saccharides [J]. Chem. Soc., Perkin Trans. 1, 2002, 803–808
[82]CORNELLA I, KELLY T R. Synthesis of Porritoxin [J]. Org. Chem, 2004, 69, 2191-2193.
[83]MASAKATSU S, KYOKO S, KENZI K, TOSHIKAZU H, HIDEO K, ISAO I. Bilayer Formation and Its Spectral Behavior of Double-Chain Amphiphiles Having CinnamateUnits [J].Langmuir,1996, 12: 2785-2790
[84]R BABUGU, J R. LAKOWICZ, C D GEDDES. Excitation and emission wavelength ratiometric cyanide-sensitive probes for physiological sensing [J].Analytical Biochemistry,2004, 327:82-90.
[85]NICOLAS D C, MAURICIO R. P, KIRK S S , JOSEPH R L. Saccharide Detection Based on the Amplified Fluorescence Quenching of a Water-Soluble Poly(phenylene ethynylene) by a Boronic Acid Functionalized Benzyl Viologen Derivative [J]. Langmuir, 2002, 18:7785-7787
[86]H S CAO, TOM M C, MICHAEL D H. Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8 -naphthalenedicarboximides [J]. Org. Chem., 2004, 69:2959- 2966
[87]JAMES T D, K R A SAMANKUMARA SANDANAYAKE, RITSUKO IGUCHI, SEIJI SHINKA. Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine [J]. Am. Chem. SOC., 1995, 117, 8982-8987
[88]H EGGERT, J FREDERIKSEN, C MORIN, C NORRILD. A New glucose-selective fluorescent bisboronic acid. First report of strongα-furanose complexation in aqueous solution at physiological pH [J].Org. Chem., 1999, 64, 3846-3852.
[89]M.S.FLEMING, D.R.WAL. Nanosphere?Microsphere Assembly: Methods for Core?Shell Materials Preparation [J].Chem.Mater,2001,13,2210
[90] RAQUEL GOMES A, JORGE PAROLA, CSAR A T LAIA, FERNANDO PINA Promoting Photochromism on Flavylium Derived 2-Hydroxychalcones in Aqueous Solutions by Addition of CTAB Micelles [J]. Phys. Chem. B, 2007, 111 (42), 12059-12065
[91]CHUANJUN LIU, ZHAIQIANG WANG, XI ZHANG Force Spectroscopy of Single-Chain Polysaccharides: Force-Induced Conformational Transition of Amylose Disappears under Environment of Micelle Solution [J]. Macromolecules, 2006, 39 (10), 3480-3483
[92]张晟卯,张治军,党鸿辛,刘维民,薛群基. TiO2 /十六烷基三甲基溴化铵有序交替层状纳米复合薄膜的制备与结构表征[J].高等学校化学学报, 2003, Vol .26, No.6 ,1136-1138
[93]李刚,高保娇,戚昌盛.采用相转移催化法制备苯二甲酰亚胺基甲基聚苯乙烯[J].高等学校化学学报, 2007, Vol .28, No.64 ,783-788
[94]张环,金朝晖,李铁龙.乙醇/水体系负载型纳米Cu/Fe二元合金的合成、改性及其还原三氯乙烯的性能[J].高等学校化学学报, 2007, Vol.28, No.12 ,2234-2238
[95]张浩然,白焱,李斌雷炳富,傅春艳.共价嫁接Ru(Ⅱ)配合物杂化材料的制备及氧气传感性能研究[J].高等学校化学学报, 2007, Vol.28, No.1, 16-20
[96] G. LI, Y. TIAN, Y. LIANG. Photoexcitation energy transfer of binary and ternary systems mediated by a bilayer membrane containing biphenyl moiety [J]. Chem. Soc. Faraday Thans., 1993, 89, 1365-1371.
[97]BENNETT L I, HOPE T B, REBECCA M R, GERARD L C. Competitive Binding Assay for Glucose Based on Glycodendrimer-Fluorophore Conjugates [J]. Anal. Chem., 2005, 77, 7039-7046