Tetrahydroxyspirobisindan
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| Structural formulas of both enantiomers | |||||||||||||||||||
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| Surname | Tetrahydroxyspirobisindan | ||||||||||||||||||
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| Molecular formula | C 21 H 24 O 4 | ||||||||||||||||||
| Brief description |
beige to light brown solid |
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| properties | |||||||||||||||||||
| Molar mass | 340.41 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
> 300 ° C |
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| solubility |
good in methanol |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Tetrahydroxyspirobisindan is a chemical compound belonging to the group of polycyclic aromatic spiro compounds .
Isomerism
The structure of Tetrahydroxyspirobisindan is by the sp 3 - hybridization constructed of the spiro carbon rigidly and substantially at right angles. The compound is chiral and, due to its synthesis, is usually present as a racemate (1: 1 mixture) of two enantiomers .
The two enantiomers are easily accessible by resolution .
Other properties
The rotation of the two enantiomers is + 44 ° and −44 ° at 26 ° C and 589 nm ( c = 1 in methanol ). Racemization can only take place by destroying the structure. Tetrahydroxyspirobisindan tends to oxidize rapidly up to dark orange colored tetraoxols when in contact with light and oxygen .
Extraction and presentation
Tetrahydroxyspirobisindan is produced in moderate yields by the condensation of acetone with pyrocatechol , catalyzed by aqueous concentrated hydrogen halide solutions . Mechanistically, the aldol reaction of three acetone molecules is first postulated, which are then substituted onto the catechols in a Friedel-Crafts alkylation .
use
- By substituting 1,2,4,5-tetrafluoro-substituted aromatics as comonomers, linear and cyclic polymers can be produced. These are characterized by a rigid molecular structure. The spongy, rigid polymers are known as Polymers of Intrinsic Microporosity ( PIM ) and are suitable, among other things, for the filtration and separation of gas mixtures
- The application of enantiomerically pure derivatives of tetrahydroxyspirobisindan for use in liquid crystal displays as chiral dopants is described
- The use of tetrahydroxyspirobisindane derivatives as UV stabilizers in photographic layers is described
Individual evidence
- ↑ a b Material Data Sheet 5,5 ', 6,6'-tetrahydroxy-3,3,3', 3'-tetramethyl-1,1'-spirobisindan , Organica Fine Chemicals GmbH Wolfen, accessed on 25 May 2012 found.
- ↑ a b c Datasheet Tetrahydroxyspirobisindan from AlfaAesar, accessed on May 18, 2012 ( PDF )(JavaScript required) .
- ↑ J. Bjork, M. Brostrom, D. Whitcomb, Molecular and supramolecular structure of 5,5 ', 6,6'-tetrahydroxy-3,3,3', 3'-tetramethyl-1,1'-spirobisindane, tetrahydrofuran solvate , in: Journal of Chemical Crystallography , 1997 , 27 , 223-230; doi: 10.1007 / BF02575959 .
- ↑ A. Dei, L. Sorace, pH-Triggered intramolecular electron transfer in asymmetric bis-dioxolene adducts , in: Dalton Transactions , 2003 , 17 , 3382-3386; doi: 10.1039 / B307270C .
- ^ W. Baker, The condensation of catechol with acetone , in: Journal of the Chemical Society (Resumed) , 1934 , 1678-1681; doi: 10.1039 / JR9340001678 .
- ↑ M. Carta et al. Mitarb ., Novel Spirobisindanes for Use as Precursors to Polymers of Intrinsic Microporosity , in: Organic Letters , 2008 , 10 , 2641-2643; doi: 10.1021 / ol800573m .
- ↑ Patent EP1768943 : Process for preparing enantiomerically pure 1,1'-spirobiindane-6,6'-diol derivatives. Filed July 7, 2005 , published April 4, 2007 , applicant: Industrial Technology Research Institute, inventor: Thomas Robert Welter.
- ↑ Patent US4360589 : Color photographic light-sensitive materials. Applied on May 14, 1981 , published on November 23, 1982 , Applicants: Fuji Photo Film Co., Ltd., Inventors: Tetsuro Kojima, Masakazu Morigaki, Tsutomu Hamaoka, Satoru Sawada.