메뉴 건너뛰기




Volumn 15, Issue 3, 2003, Pages 231-237

Evaluation of absolute configuration of naphthylphenyl-substituted oligosilanes by CD exciton chirality method

Author keywords

conjugation; Absolute configuration; CD exciton chirality; Oligosilane; Silicon stereochemistry

Indexed keywords

METHYL GROUP; NAPHTHYL GROUP; OLIGOMER; PHENYL GROUP; SILANE DERIVATIVE; SILICON;

EID: 0037282487     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10192     Document Type: Article
Times cited : (18)

References (53)
  • 1
    • 0000853389 scopus 로고
    • Characterization of poly(di-n-hexylsilane) in the solid state. II. Carbon-13 and silicon-29 magic-angle spinning NMR studies
    • (a) Schilling FC, Bovey FA, Lovinger AJ, Ziegler JM. Characterization of poly(di-n-hexylsilane) in the solid state. II. Carbon-13 and silicon-29 magic-angle spinning NMR studies. Macromolecules 1986;19:2660-2663.
    • (1986) Macromolecules , vol.19 , pp. 2660-2663
    • Schilling, F.C.1    Bovey, F.A.2    Lovinger, A.J.3    Ziegler, J.M.4
  • 2
    • 0026418474 scopus 로고
    • Poly(n-butyl-n-hexylsilylene): A liquidcrystalline polysilane
    • (b) Asuke T, West R. Poly(n-butyl-n-hexylsilylene): a liquidcrystalline polysilane. Macromolecules 1991;24:343-344.
    • (1991) Macromolecules , vol.24 , pp. 343-344
    • Asuke, T.1    West, R.2
  • 3
  • 4
    • 33750317624 scopus 로고
    • Electronic spectra of polysilanes
    • (a) Harrah LA, Ziegler JM. Electronic spectra of polysilanes. Macromolecules 1987;20:601-608.
    • (1987) Macromolecules , vol.20 , pp. 601-608
    • Harrah, L.A.1    Ziegler, J.M.2
  • 5
    • 0000899472 scopus 로고
    • Ideal exciton spectra in single- and double-screw-sense helical polysilanes
    • (b) Fujiki M. Ideal exciton spectra in single- and double-screw-sense helical polysilanes. J Am Chem Soc 1994;116:6017-6018.
    • (1994) J Am Chem Soc , vol.116 , pp. 6017-6018
    • Fujiki, M.1
  • 6
    • 0022043579 scopus 로고
    • Electro-oxidation of substituted silane high polymers
    • (a) Diaz A, Miller RD. Electro-oxidation of substituted silane high polymers. J Electrochem Soc 1985;132:834-837.
    • (1985) J Electrochem Soc , vol.132 , pp. 834-837
    • Diaz, A.1    Miller, R.D.2
  • 8
    • 0033807612 scopus 로고    scopus 로고
    • Occurrence of radical cation localization in chemically modified poly(methylphenylsilane): Poly(methylphenyl-co-4-dimethylaminophenylmethylsilane)s and poly(methylphenyl-co-4-bromophenylmethylsilane)s
    • (a) Cleij TJ, King JK, Jennesken LW. Occurrence of radical cation localization in chemically modified poly(methylphenylsilane): poly(methylphenyl-co-4-dimethylaminophenylmethylsilane)s and poly(methylphenyl-co-4-bromophenylmethylsilane)s. Chem Mater 2000;12: 84-89.
    • (2000) Chem Mater , vol.12 , pp. 84-89
    • Cleij, T.J.1    King, J.K.2    Jennesken, L.W.3
  • 9
    • 0033639761 scopus 로고    scopus 로고
    • Band gap modifications in functionalized poly(methylphenylsilanes)
    • (b) Cleij TJ, King JK, Jennesken LW. Band gap modifications in functionalized poly(methylphenylsilanes). Macromolecules 2000;33: 89-96.
    • (2000) Macromolecules , vol.33 , pp. 89-96
    • Cleij, T.J.1    King, J.K.2    Jennesken, L.W.3
  • 10
    • 33845556639 scopus 로고
    • Phenylmethylpolysilanes: Formable silane copolymers with potential semiconducting properties
    • (a) West R, David LD, Djurovich PI, Stearley KL, Shinivasan KSV, Yu H. Phenylmethylpolysilanes: formable silane copolymers with potential semiconducting properties. J Am Chem Soc 1981;103:7352-7354.
    • (1981) J Am Chem Soc , vol.103 , pp. 7352-7354
    • West, R.1    David, L.D.2    Djurovich, P.I.3    Stearley, K.L.4    Shinivasan, K.S.V.5    Yu, H.6
  • 12
    • 0024733839 scopus 로고
    • Polysilane high polymers
    • (a) Miller RD, Michl J. Polysilane high polymers. Chem Rev 1989;89: 1359-1310.
    • (1989) Chem Rev , vol.89 , pp. 1359-1310
    • Miller, R.D.1    Michl, J.2
  • 14
    • 0035137776 scopus 로고    scopus 로고
    • Self-organized oligosilanes; a new class of organic hole-transport materials
    • (a) Okumoto H, Yatabe T, Shimomura M, Kaito A, Minami N, Tanabe Y. Self-organized oligosilanes; a new class of organic hole-transport materials. Adv Mater 2001;13:72-76.
    • (2001) Adv Mater , vol.13 , pp. 72-76
    • Okumoto, H.1    Yatabe, T.2    Shimomura, M.3    Kaito, A.4    Minami, N.5    Tanabe, Y.6
  • 15
    • 0035867159 scopus 로고    scopus 로고
    • Hole transport properties of self-organized oligosilane film in a polycrystalline and a mesophase
    • (b) Okumoto H, Yatabe T, Peng J, Kaito A, Minami N. Hole transport properties of self-organized oligosilane film in a polycrystalline and a mesophase. Synth Met 2001;121:1507-1508.
    • (2001) Synth Met , vol.121 , pp. 1507-1508
    • Okumoto, H.1    Yatabe, T.2    Peng, J.3    Kaito, A.4    Minami, N.5
  • 17
    • 0032590837 scopus 로고    scopus 로고
    • Structure of vacuum-deposited permethyldecasilane thin films
    • (b) Ichino Y, Minami N, Yatabe T, Shimomura M, Kaito A. Structure of vacuum-deposited permethyldecasilane thin films. Synth Met 1999; 101:637-638.
    • (1999) Synth Met , vol.101 , pp. 637-638
    • Ichino, Y.1    Minami, N.2    Yatabe, T.3    Shimomura, M.4    Kaito, A.5
  • 20
    • 0002550270 scopus 로고    scopus 로고
    • Exciton chirality methods: Principles and applications
    • Berova N, Nakanishi K, Woody RW, editors. New York: Wiley-VCH
    • (b) Berova N, Nakanishi K. Exciton chirality methods: principles and applications. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley-VCH; 2000. p 337-392.
    • (2000) Circular Dichroism: Principles and Applications , pp. 337-392
    • Berova, N.1    Nakanishi, K.2
  • 23
    • 0000618363 scopus 로고
    • Absolute stereochemistry and chiroptical properties of chiral tribenzotriptycene and benzotriptycenes
    • (a) Harada N, Tamai Y, Takuma Y, Uda H. Absolute stereochemistry and chiroptical properties of chiral tribenzotriptycene and benzotriptycenes. J Am Chem Soc 1980;102;501-506.
    • (1980) J Am Chem Soc , vol.102 , pp. 501-506
    • Harada, N.1    Tamai, Y.2    Takuma, Y.3    Uda, H.4
  • 24
    • 0001461426 scopus 로고
    • Unique UV-Vis absorption and circular dichroic exciton-split spectra of a chiral biscyanine dye: Origin and nature
    • (b) Berova N, Gaegiulo D, Derguini F, Nakanishi K, Harada N. Unique UV-Vis absorption and circular dichroic exciton-split spectra of a chiral biscyanine dye: origin and nature. J Am Chem Soc 1993;115:4769-4775.
    • (1993) J Am Chem Soc , vol.115 , pp. 4769-4775
    • Berova, N.1    Gaegiulo, D.2    Derguini, F.3    Nakanishi, K.4    Harada, N.5
  • 25
  • 26
    • 0030050523 scopus 로고    scopus 로고
    • Acyclic 1,2-/1,3-mixed pentols. Synthesis and general trends in bichromophoric exciton coupled circular dichroic spectra
    • (a) Rele D, Zhao N, Nakanishi K, Berova N. Acyclic 1,2-/1,3-mixed pentols. Synthesis and general trends in bichromophoric exciton coupled circular dichroic spectra. Tetrahedron 1996;52:2759-2776.
    • (1996) Tetrahedron , vol.52 , pp. 2759-2776
    • Rele, D.1    Zhao, N.2    Nakanishi, K.3    Berova, N.4
  • 27
    • 0001290748 scopus 로고
    • A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate system
    • (b) Harada N, Saito A, Ono H, Gawronski J, Gawronska K, Sugioka T, Uda H, Kuriki T. A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate system. J Am Chem Soc 1991;113:3842-3850.
    • (1991) J Am Chem Soc , vol.113 , pp. 3842-3850
    • Harada, N.1    Saito, A.2    Ono, H.3    Gawronski, J.4    Gawronska, K.5    Sugioka, T.6    Uda, H.7    Kuriki, T.8
  • 28
    • 0000006931 scopus 로고
    • General method for determining absolute configurations of acyclic allylic alcohols
    • (c) Gonnella NC, Nakanishi K, Martin V, Sharpless B. General method for determining absolute configurations of acyclic allylic alcohols. J Am Chem Soc 1982;104:3775-3776.
    • (1982) J Am Chem Soc , vol.104 , pp. 3775-3776
    • Gonnella, N.C.1    Nakanishi, K.2    Martin, V.3    Sharpless, B.4
  • 29
    • 0035977207 scopus 로고    scopus 로고
    • A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfonyl-1-alkanols using the CD exciton chirality method
    • (d) Weckerle B, Schreier P, Humpf HU. A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfonyl-1-alkanols using the CD exciton chirality method. J Org Chem 2001;66:8160-8164.
    • (2001) J Org Chem , vol.66 , pp. 8160-8164
    • Weckerle, B.1    Schreier, P.2    Humpf, H.U.3
  • 30
    • 0000248841 scopus 로고
    • The ultraviolet spectra of some polysilanes
    • (a) Sakurai H, Kumada M. The ultraviolet spectra of some polysilanes. Bull Chem Soc Jpn 1964;1894-1895.
    • (1964) Bull Chem Soc Jpn , pp. 1894-1895
    • Sakurai, H.1    Kumada, M.2
  • 31
    • 0002121166 scopus 로고
    • Catenated organic compounds of silicon, germanium, tin, and lead
    • (b) Gilman H, Atwell WH, Cartledge FK. Catenated organic compounds of silicon, germanium, tin, and lead. Adv Organomet Chem 1966;4:1-89.
    • (1966) Adv Organomet Chem , vol.4 , pp. 1-89
    • Gilman, H.1    Atwell, W.H.2    Cartledge, F.K.3
  • 32
  • 33
    • 0001774544 scopus 로고    scopus 로고
    • Stereospecific formation of optically active trialkylsilyllithiums and their configurational stability
    • Omote M, Tokita T, Shimizu Y, Imae I, Shirakawa E, Kawakami Y. Stereospecific formation of optically active trialkylsilyllithiums and their configurational stability. J Organometal Chem 2000;611:20-25.
    • (2000) J Organometal Chem , vol.611 , pp. 20-25
    • Omote, M.1    Tokita, T.2    Shimizu, Y.3    Imae, I.4    Shirakawa, E.5    Kawakami, Y.6
  • 35
    • 0013457944 scopus 로고
    • The SN2-Si and SNi-Si mechanisms: Common reaction paths for monofunctional organosilicon compounds
    • (b) Sommer LH. The SN2-Si and SNi-Si mechanisms: Common reaction paths for monofunctional organosilicon compounds. Intra-Science Chem Rept 1973;7:1-38.
    • (1973) Intra-Science Chem Rept , vol.7 , pp. 1-38
    • Sommer, L.H.1
  • 36
    • 33947481392 scopus 로고
    • Stereochemistry of asymmetric silicon. I. Relative and absolute configurations of optically active α-naphthylphenylmethylsilanes
    • (c) Sommer LH, Frye CL, Parker GA, Michael KW. Stereochemistry of asymmetric silicon. I. Relative and absolute configurations of optically active α-naphthylphenylmethylsilanes. J Am Chem Soc 1964;86:3271-3276.
    • (1964) J Am Chem Soc , vol.86 , pp. 3271-3276
    • Sommer, L.H.1    Frye, C.L.2    Parker, G.A.3    Michael, K.W.4
  • 37
    • 0000376715 scopus 로고
    • Cleavage of symmetrically substituted disilanes by lithium in tetrahydrofuran
    • (a) Gilman H, Lichtenwalter GD. Cleavage of symmetrically substituted disilanes by lithium in tetrahydrofuran. J Am Chem Soc 1958;80: 608-611.
    • (1958) J Am Chem Soc , vol.80 , pp. 608-611
    • Gilman, H.1    Lichtenwalter, G.D.2
  • 38
    • 0029471604 scopus 로고
    • Silicon derivatives of the metals of groups 1 and 2
    • (b) Lickiss PD, Smith CM. Silicon derivatives of the metals of groups 1 and 2. Coor Chem Rev 1995;145;75-124.
    • (1995) Coor Chem Rev , vol.145 , pp. 75-124
    • Lickiss, P.D.1    Smith, C.M.2
  • 40
    • 0034525770 scopus 로고    scopus 로고
    • Lithiosilanes and their application to the synthesis of polysilane dendrimers
    • (d) Sekiguchi A, Lee VY, Nanjo M. Lithiosilanes and their application to the synthesis of polysilane dendrimers. Coor Chem Rev 2000;210:11-45.
    • (2000) Coor Chem Rev , vol.210 , pp. 11-45
    • Sekiguchi, A.1    Lee, V.Y.2    Nanjo, M.3
  • 41
    • 0013458685 scopus 로고
    • Stereochemistry of asymmetric silicon. XI. Optical rotatory dispersion and circular dichroism of α-NpPhMeSi*X compounds
    • Sommer LH, McLick J. Stereochemistry of asymmetric silicon. XI. Optical rotatory dispersion and circular dichroism of α-NpPhMeSi*X compounds. J Am Chem Soc 1969;91:2001-2010.
    • (1969) J Am Chem Soc , vol.91 , pp. 2001-2010
    • Sommer, L.H.1    McLick, J.2
  • 42
    • 0342780126 scopus 로고
    • Nature of the electronic interactions in aryl-substituted polysilanes
    • Pitt CG, Carey RN, Toren EC Jr. Nature of the electronic interactions in aryl-substituted polysilanes. J Am Chem Soc 1972;94:3806-3811.
    • (1972) J Am Chem Soc , vol.94 , pp. 3806-3811
    • Pitt, C.G.1    Carey, R.N.2    Toren E.C., Jr.3
  • 43
    • 36849141854 scopus 로고
    • Classification of spectra of cata-condensed hydrocarbons
    • (a) Platt JR. Classification of spectra of cata-condensed hydrocarbons. J Chem Phys 1949;17:484-495.
    • (1949) J Chem Phys , vol.17 , pp. 484-495
    • Platt, J.R.1
  • 44
    • 0000621438 scopus 로고    scopus 로고
    • Changes in the electronic transitions of aromatic hydrocarbons on chemical substitution. II. Application of perturbation theory to substituted-benzene spectra
    • 1061
    • (b) Petruska J. Changes in the electronic transitions of aromatic hydrocarbons on chemical substitution. II. Application of perturbation theory to substituted-benzene spectra. J Chem Phys 1061;34:1120-1136.
    • J Chem Phys , vol.34 , pp. 1120-1136
    • Petruska, J.1
  • 45
    • 0033979977 scopus 로고    scopus 로고
    • Microscale determination of the absolute configuration of α-arylsubstituted alcohols by the CD exciton chirality methods
    • Adam W, Lukacs Z, Viebach K, Humpf HU, Saha-Möller CR, Schreier P. Microscale determination of the absolute configuration of α-arylsubstituted alcohols by the CD exciton chirality methods. J Org Chem 2000;65:186-190.
    • (2000) J Org Chem , vol.65 , pp. 186-190
    • Adam, W.1    Lukacs, Z.2    Viebach, K.3    Humpf, H.U.4    Saha-Möller, C.R.5    Schreier, P.6
  • 46
    • 0000833148 scopus 로고    scopus 로고
    • Mechanistic aspects of the photochemistry of organosilicon compounds
    • Rappoport Z, Apeloig Y, editors. New York: John Wiley & Sons
    • (a) Kira M, Miyazawa T. Mechanistic aspects of the photochemistry of organosilicon compounds. In: Rappoport Z, Apeloig Y, editors. The chemistry of organic silicon compounds. New York: John Wiley & Sons; 1998. p 1311-1337.
    • (1998) The Chemistry of Organic Silicon Compounds , pp. 1311-1337
    • Kira, M.1    Miyazawa, T.2
  • 47
    • 0037140750 scopus 로고    scopus 로고
    • Intramolecular charge-transfer process of jet-cooled (p-cyanopheny)pentamethyldisilane: Roles of the torsional motion and the Si-Si bond change
    • (b) Ishikawa H, Shimanuki Y, Sugiyama M, Tajima Y, Kira M, Mikami N. Intramolecular charge-transfer process of jet-cooled (p-cyanopheny)pentamethyldisilane: roles of the torsional motion and the Si-Si bond change. J Am Chem Soc 2002;124:6220-6230.
    • (2002) J Am Chem Soc , vol.124 , pp. 6220-6230
    • Ishikawa, H.1    Shimanuki, Y.2    Sugiyama, M.3    Tajima, Y.4    Kira, M.5    Mikami, N.6
  • 48
    • 0001698311 scopus 로고
    • σπ* orthogonal intramolecular charge-transfer (OICT) excited states and photoreaction mechanism of trifluoromethyl-substituted phenyldisilanes
    • (a) Kira M, Miyazawa T, Sugiyama H, Yamaguchi M, Sakurai H. σπ* orthogonal intramolecular charge-transfer (OICT) excited states and photoreaction mechanism of trifluoromethyl-substituted phenyldisilanes. J Am Chem Soc 1993;115:3116-3124.
    • (1993) J Am Chem Soc , vol.115 , pp. 3116-3124
    • Kira, M.1    Miyazawa, T.2    Sugiyama, H.3    Yamaguchi, M.4    Sakurai, H.5
  • 49
    • 0001009718 scopus 로고
    • 1(σπ*) orthogonal intramolecular charge-transfer states
    • 1(σπ*) orthogonal intramolecular charge-transfer states. J Phys Chem 1990;94:1837-1843.
    • (1990) J Phys Chem , vol.94 , pp. 1837-1843
    • Sakurai, H.1    Sugiyama, H.2    Kira, M.3
  • 50
    • 0013399860 scopus 로고    scopus 로고
    • Fujitsu Co. Japan
    • (a) WinMOPAC Ver. 3.0 Pro; Fujitsu Co. Japan, 2000.
    • (2000) WinMOPAC Ver. 3.0 Pro
  • 51
    • 0013356537 scopus 로고    scopus 로고
    • note
    • All calculations were performed with PM3 method and optimized using the Eigenvector Following Routine (keyword EF, Precise) until a GNOME = 0.05.
  • 53
    • 0013358496 scopus 로고
    • Stereochemistry of asymmetric silicon. XXI. Optical rotatory dispersion and circular dichroism of asymmetric disilane Ph3SiSi*X(Ph) (Me) and a case of aberrant Cotton effect behavior
    • Sommer LH, Rosborough KT, McLick J. Stereochemistry of asymmetric silicon. XXI. Optical rotatory dispersion and circular dichroism of asymmetric disilane Ph3SiSi*X(Ph) (Me) and a case of aberrant Cotton effect behavior. J Am Chem Soc 1972;94:4217-4222.
    • (1972) J Am Chem Soc , vol.94 , pp. 4217-4222
    • Sommer, L.H.1    Rosborough, K.T.2    McLick, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.