Compositions – Light transmission modifying compositions
Patent
1997-07-18
1999-11-30
Tucker, Philip
Compositions
Light transmission modifying compositions
252585, 252587, 252589, 568 20, 568 28, 568 33, 568326, 558427, F21V 900, F21V 914, C07C 49115, C07C25500
Patent
active
059937009
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Prior workers have shown a number of approximately disk shaped aromatic hydrocarbons that are approximately symmetrically substituted with numerous chains form ordered liquids called discotic mesophases. In some of these, called columnar discotic mesophases, molecules stack in cylindrical columns in which planes of aromatic rings are approximately perpendicular to the cylindrical axis.
Yamamura and Tabushi [Tetrahedron Let. (1988) Vol 29: pp.1797-1798] prepared biphenanthryl, but did not obtain it optically active and did not record any chiroptical properties.
SUMMARY OF THE INVENTION
This invention provides an aggregate of a compound capable of forming helical structures such that the aggregate is capable of achieving a specific rotation of at least 100,000.degree. for plane polarized light having a wavelength of 589 nm.
The aggregate may be in n eat form.
This invention further provides an aggregate wherein the compound has the structure: ##STR1## wherein rings A and B represent independent electron accepting ring systems and wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and are H, substituted or unsubstituted, saturated or unsaturated alkyl, alkenyl, cycloalkyl, aryl, or arylalkyl --SR, --NRR', --OR, --OC(O)R, SC(O)R, --SCR, wherein R and R' are independently substituted or unsubstituted, saturated or unsaturated alkyl, alkenyl, cycloalkyl, aryl, or arylalkyl. The compound of claim 1 wherein ring A and ring B can be the same or different and are a substituted or unsubstituted hydrocarbon or heteratomic ring system having between 5 and 9 atoms in the ring.
This invention also provides thin films comprising the above aggregates or a suitable derivative thereof.
This invention further comprises liquid crystal display devices and non-linear optical devices comprising the above aggregates or a suitable derivative thereof.
Finally, this invention provides a method for achieving high order non-linear optical responses utilizing the above aggregates or a suitable derivative thereof.
BRIEF DESCRIPTION OF THE FIGURES
FIG. 1--Structure of dodecyloxy-substituted [6]helicene bis-quinone.
FIG. 2--Synthesis of optically active dodecyloxy-substituted [6]helicene bis-quinone shown in FIG. 1 and synthesis of related intermediate compounds.
FIG. 3--Reaction mechanism for the production of the dodecyloxy-substituted [6]helicene bis-quinone.
FIG. 4--CD spectra of n-dodecane solutions of the compound of FIG. 1 in varying concentrations and cell lengths: (-) c=2.1.times.10.sup.-2 M, l=0.01 mm; (--) c=2.1.times.10.sup.- 4 M, l=1 mm; (.sup....) c=1.3.times.10.sup.-5 M, l=10 mm.
FIG. 5--Structure of hexaether diacetate, (HEDA) starting material for synthesis of the compound of FIG. 1.
FIG. 6--Aggregates of the compound shown in FIG. 1.
FIG. 7(a) Circular dichroism spectra for solutions of the compound showing FIG. 1 in n-dodecane.
FIG. 7(b) UV absorption spectra for solutions of the compound shown in FIG. 1 in n-dodecane.
FIG. 7(c) Fluorescence emission spectra for solutions of the compound shown in FIG. 1 in n-dodecane.
DETAILED DESCRIPTION
This invention provides an aggregate of a compound capable of forming helical structures such that the aggregate is capable of rotating plane polarized light having a wavelength of 589 nm at least 100,000.degree..
This invention further provides the above aggregate in neat form. As used herein, "in neat form" means where there is no solvent.
This invention also provides the above aggregate wherein the compound has the structure: ##STR2## wherein rings A and B represent independent electron accepting ring systems and wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and are H, substituted or unsubstituted, saturated or unsaturated alkyl, alkenyl, cycloalkyl, aryl, or arylalkyl --SR, --NRR', --OR, --OC(O)R, SC(O)R, --SCR, wherein R and R' are independently substituted or unsubstituted, saturated or unsaturated alkyl, alkenyl, cycloalkyl,
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Song, X. et al., (1994) "trans-Stilbene Aggregates in Microheterogeneous Media: Evidence for a Chiral Cyclic Supramolecular Unit", J. Am. Chem. Soc. , 116: 10340-10341.
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Katz Thomas J.
Nuckolls Colin P.
The Trustees of Columbia University in the City of New York
Tucker Philip
White John P.
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