Thermal properties of monosubstituted ferrocene derivatives: A series of new ferrocenomesogens
The preparation of a series of 1-substituted ferrocene derivatives is described. The structure of the substituent was varied systematically in order to determine the structural limits within which mesogenic behaviour is retained. The compounds are particularly useful for stabilizing the nematic phas...
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| Veröffentlicht in: | Perkin transactions. 2 H. 3; S. 399 - 409 |
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| Format: | Journal Article |
| Sprache: | Englisch |
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Royal Soc Chemistry
1997
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| ISSN: | 0300-9580 |
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| Abstract | The preparation of a series of 1-substituted ferrocene derivatives is described. The structure of the substituent was varied systematically in order to determine the structural limits within which mesogenic behaviour is retained. The compounds are particularly useful for stabilizing the nematic phase, the range of which was increased substantially by extending the aromatic core of the substituent. Selective lateral fluorination was successfully used to lower the nematic temperatures as well as to suppress any smectic phases. Derivatives with no more than two rings in the core only display the crystal smectic B phase. The significance of substituents on the cyclopentadienyl rings is discussed with reference to their electronic properties and their effect on the stability of the compounds. |
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| AbstractList | The preparation of a series of 1-substituted ferrocene derivatives is described. The structure of the substituent was varied systematically in order to determine the structural limits within which mesogenic behaviour is retained. The compounds are particularly useful for stabilizing the nematic phase, the range of which was increased substantially by extending the aromatic core of the substituent. Selective lateral fluorination was successfully used to lower the nematic temperatures as well as to suppress any smectic phases. Derivatives with no more than two rings in the core only display the crystal smectic B phase. The significance of substituents on the cyclopentadienyl rings is discussed with reference to their electronic properties and their effect on the stability of the compounds. |
| Author | Loubser, C Imrie, C |
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| DOI | 10.1039/a600739b |
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| Keywords | ESTER THERMOTROPIC LIQUID-CRYSTALS PHASE MOLECULAR-STRUCTURE BEHAVIOR COMPLEXES DIESTERS |
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| References | VAUCHIER, C (WOS:A1989AG20600011) 1989; 5 GRAY, GW (WOS:A19667913300009) 1966; 1 BHATT, J (WOS:A1988Q886600025) 1988 BEHRENS, U (WOS:A1979HV99400008) 1979; 182 NESMEYANOV, AN (WOS:A19639711A00046) 1963; 149 CRABTREE RH (WOS:A1997WN48100002.5) 1988 KHAN, MA (WOS:A1989AG20600024) 1989; 5 SINGH, P (WOS:A1991ET47900003) 1991; 9 DESCHENAUX, R (WOS:A1994NM54300006) 1994; 4 LOUBSER, C (WOS:A1995RQ99800002) 1995; 5 NESMEYANOV AN (WOS:A1997WN48100002.28) 1967; 1 CHAMBERS, M (WOS:A1989AG20600012) 1989; 5 ROSENBLUM M (WOS:A1997WN48100002.31) 1965 GALYAMETDINOV, YG (WOS:A1994QE27600036) 1994; 43 WERNER, A (WOS:A1994MY78200001) 1994 DESCHENAUX R (WOS:A1997WN48100002.6) 1995 IMRIE, C (WOS:A1994PJ67500068) 1994 GRAY GW (WOS:A1997WN48100002.14) 1984 TOYNE KJ (WOS:A1997WN48100002.33) 1987; 22 GALYAMETDINOV, YG (WOS:A1990FU81700023) 1990; 39 NESMEYANOV AN (WOS:A1997WN48100002.27) 1965; 9 NESMEYAN.AN (WOS:A1970H797600025) 1970; 194 NESMEYANOV, AN (WOS:A19649746A00042) 1964; 155 ADAMS, H (WOS:A1994NC52300006) 1994; 16 ZAKHARKIN, LI (WOS:A1982QA33300011) 1982; 38 KHAND, IU (WOS:A1989CA33100033) 1989 DESCHENAUX, R (WOS:A1995RQ44600013) 1995; 78 NESMEYANOV AN (WOS:A1997WN48100002.29) 1959; 17 DESCHENAUX, R (WOS:A1993KV90300009) 1993; 76 MALTHETE, J (WOS:A1976CT89000001) 1976; 34 LEWTHWAITE, RA (WOS:A1992HD53300020) 1992; 2 OSGERBY, JM (WOS:A19614205B00075) 1961 HANASAKI, T (WOS:A1993MN00800030) 1993; 237 GALYAMETDINOV ON (WOS:A1997WN48100002.10) 1995 IMRIE, C (WOS:A1995QQ52200009) 1995; 9 LOUBSER, C (WOS:A1993KH57000008) 1993; 5 |
| References_xml | – volume: 182 start-page: 89 year: 1979 ident: WOS:A1979HV99400008 article-title: TRANSITION-METAL FULVENE COMPLEXES .14. CRYSTAL AND MOLECULAR-STRUCTURE OF FERROCENYLDIPHENYLCARBENIUM TETRAFLUOROBORATE - FULVENE-IRON COMPLEX publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY – start-page: 2075 year: 1989 ident: WOS:A1989CA33100033 article-title: FERROCENE DERIVATIVES .24. SYNTHESIS OF DIHYDRO-2-PYRINDINES AND DIHYDRO-3H-2-CYCLOPENT[C]AZEPINES BY PHOTOLYSIS OF THEIR CYCLOPENTADIENYLIRON DERIVATIVES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – year: 1965 ident: WOS:A1997WN48100002.31 publication-title: CHEM IRON GROUP META – volume: 155 start-page: 1130 year: 1964 ident: WOS:A19649746A00042 article-title: PHOTOLYSIS OF FERROCENE DERIVATIVES publication-title: DOKLADY AKADEMII NAUK SSSR – volume: 22 start-page: CH2 year: 1987 ident: WOS:A1997WN48100002.33 publication-title: CRITICAL REPORTS APP – volume: 78 start-page: 1215 year: 1995 ident: WOS:A1995RQ44600013 article-title: CRYSTAL SMECTIC-B PHASE FROM A MESOMORPHIC FERROCENE DERIVATIVE publication-title: HELVETICA CHIMICA ACTA – volume: 5 start-page: 285 year: 1989 ident: WOS:A1989AG20600024 article-title: X-RAY-DIFFRACTION STUDIES OF MESOMORPHIC FERROCENE DIESTERS publication-title: LIQUID CRYSTALS – volume: 5 start-page: 1107 year: 1995 ident: WOS:A1995RQ99800002 article-title: UNUSUAL ORIENTATIONAL BEHAVIOR OF LIQUID-CRYSTALS - INVESTIGATION OF THE EFFECT OF DIPOLAR INTERACTIONS ON THE FERROELECTRIC PROPERTIES publication-title: JOURNAL OF MATERIALS CHEMISTRY – volume: 39 start-page: 2235 year: 1990 ident: WOS:A1990FU81700023 article-title: THE 1ST HETERONUCLEAR LIQUID-CRYSTAL METAL-COMPLEX publication-title: BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE – volume: 43 start-page: 887 year: 1994 ident: WOS:A1994QE27600036 article-title: LIQUID-CRYSTALLINE HETERONUCLEAR COMPLEXES WITH A FERROCENE-CONTAINING SCHIFFS BASE publication-title: RUSSIAN CHEMICAL BULLETIN – start-page: 365 year: 1994 ident: WOS:A1994MY78200001 article-title: A LIQUID-CRYSTALLINE [3]FERROCENOPHANE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – start-page: 4604 year: 1961 ident: WOS:A19614205B00075 article-title: FERROCENE DERIVATIVES .9. SOME DISUBSTITUTED DERIVATIVES publication-title: JOURNAL OF THE CHEMICAL SOCIETY – start-page: 358 year: 1995 ident: WOS:A1997WN48100002.10 publication-title: IAN SSSR KH – volume: 237 start-page: 329 year: 1993 ident: WOS:A1993MN00800030 article-title: SYNTHESES AND PHYSICAL-PROPERTIES OF FERROCENE DERIVATIVES .2. LIQUID CRYSTALLINITY AND MULTIPLE MELTING BEHAVIOR OF FERROCENE DERIVATIVES publication-title: MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS – volume: 1 year: 1967 ident: WOS:A1997WN48100002.28 publication-title: METHODS ELEMENTO ORG – volume: 9 start-page: 75 year: 1995 ident: WOS:A1995QQ52200009 article-title: THE STABILITY OF FERROCENYLMETHYL DERIVATIVES - FURTHER ATTEMPTS TO SYNTHESIZE FERROCENYLACETONE publication-title: APPLIED ORGANOMETALLIC CHEMISTRY – volume: 16 start-page: 643 year: 1994 ident: WOS:A1994NC52300006 article-title: THE SYNTHESIS OF LATERALLY FLUORINATED ALKOXYSTILBAZOLES AND SOME OF THEIR MESOGENIC COMPLEXES WITH IR(I) - THE MOLECULAR-STRUCTURE OF TRANS-4-UNDECYCLOXY-3-FLUORO-4'-STILBAZOLE publication-title: LIQUID CRYSTALS – start-page: CH5 year: 1988 ident: WOS:A1997WN48100002.5 publication-title: ORGANOMETALLIC CHEM – volume: 4 start-page: 679 year: 1994 ident: WOS:A1994NM54300006 article-title: 1,3-DISUBSTITUTED FERROCENE-CONTAINING THERMOTROPIC LIQUID-CRYSTALS OF FORM (ETA-5-C5H5)FE[(ETA-5-C5H3)-1,3-(CO2C6H4CO2C6H4OCNH2N+1)2] publication-title: JOURNAL OF MATERIALS CHEMISTRY – volume: 2 start-page: 119 year: 1992 ident: WOS:A1992HD53300020 article-title: SYNTHESIS AND TRANSITION-TEMPERATURES OF SOME NOVEL, CHIRAL NEMATIC, LATERALLY ATTACHED, SIDE-CHAIN, SILOXANE POLYMERS publication-title: JOURNAL OF MATERIALS CHEMISTRY – volume: 5 start-page: 153 year: 1989 ident: WOS:A1989AG20600012 article-title: LATERALLY FLUORINATED PHENYL BIPHENYLCARBOXYLATES - VERSATILE COMPONENTS FOR FERROELECTRIC SMECTIC-C MIXTURES publication-title: LIQUID CRYSTALS – volume: 194 start-page: 1332 year: 1970 ident: WOS:A1970H797600025 article-title: PHOTOLYSIS OF IODEMETHYLATE 2-(CHLORINE)-A-PYRIDILFERROCENE publication-title: DOKLADY AKADEMII NAUK SSSR – volume: 5 start-page: 141 year: 1989 ident: WOS:A1989AG20600011 article-title: NEW BIFLUORINATED LIQUID-CRYSTAL COMPOUNDS WITH BROAD MESOMORPHIC RANGES publication-title: LIQUID CRYSTALS – volume: 9 start-page: 1694 year: 1965 ident: WOS:A1997WN48100002.27 publication-title: IAN SSSR KH – volume: 149 start-page: 1354 year: 1963 ident: WOS:A19639711A00046 article-title: PHOTOLYSIS OF ALPHA-PYRIDYLFERROCENE SALTS publication-title: DOKLADY AKADEMII NAUK SSSR – volume: 17 start-page: 13 year: 1959 ident: WOS:A1997WN48100002.29 publication-title: TETRAHEDRON LETT – volume: 5 start-page: 45 year: 1993 ident: WOS:A1993KH57000008 article-title: THE SYNTHESIS AND CRYSTAL-STRUCTURE OF A LIQUID-CRYSTALLINE ESTER OF 4-CARBOXYPHENYLFERROCENE publication-title: ADVANCED MATERIALS – volume: 1 start-page: 333 year: 1966 ident: WOS:A19667913300009 article-title: INFLUENCE OF MOLECULAR STRUCTURE ON LIQUID CRYSTALLINE PROPERTIES publication-title: MOLECULAR CRYSTALS – start-page: CH9 year: 1995 ident: WOS:A1997WN48100002.6 publication-title: FERROCENES HOMOGENEO – volume: 76 start-page: 865 year: 1993 ident: WOS:A1993KV90300009 article-title: 1,1'-DISUBSTITUTED FERROCENE-CONTAINING THERMOTROPIC LIQUID-CRYSTALS OF STRUCTURE [FE((ETA-5-C5H4)COOC6H4XC6H4OCNH2N+1)2] (X = OOC OR COO) - INFLUENCE OF THE ORIENTATION OF THE CENTRAL ESTER FUNCTION ON THE MESOGENIC PROPERTIES publication-title: HELVETICA CHIMICA ACTA – start-page: 2159 year: 1994 ident: WOS:A1994PJ67500068 article-title: A LIQUID-CRYSTALLINE FERROCENE DERIVATIVE WITH A CHIRAL SMECTIC C-PHASE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 9 start-page: 19 year: 1991 ident: WOS:A1991ET47900003 article-title: FERROCENE-BASED LIQUID-CRYSTALLINE COMPOUNDS publication-title: LIQUID CRYSTALS – volume: 38 start-page: 3515 year: 1982 ident: WOS:A1982QA33300011 article-title: SYNTHESIS AND SOME REACTIONS OF CARBENIUM IONS OF NEW TYPES STABILIZED WITH PI-CYCLOPENTADIENYL-PI-(3)-1,2-DICARBOLLYL-IRON (II) GROUP - STRUCTURE OF 3-PI-C5H5FEII-PI-1,2-C2B9HBAR10-1-C+HC6H5 publication-title: TETRAHEDRON – volume: 34 start-page: 117 year: 1976 ident: WOS:A1976CT89000001 article-title: MESOMORPHIC DERIVATIVES OF FERROCENE publication-title: MOLECULAR CRYSTALS AND LIQUID CRYSTALS – start-page: 1439 year: 1988 ident: WOS:A1988Q886600025 article-title: NOVEL FERROCENE DIESTERS WITH LIQUID-CRYSTAL PROPERTIES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – year: 1984 ident: WOS:A1997WN48100002.14 publication-title: SMECTIC LIQUID CRYST |
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| Snippet | The preparation of a series of 1-substituted ferrocene derivatives is described. The structure of the substituent was varied systematically in order to... |
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| Title | Thermal properties of monosubstituted ferrocene derivatives: A series of new ferrocenomesogens |
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