GB2238541A - Organic materials for use in optical processing - Google Patents

Organic materials for use in optical processing Download PDF

Info

Publication number
GB2238541A
GB2238541A GB8927206A GB8927206A GB2238541A GB 2238541 A GB2238541 A GB 2238541A GB 8927206 A GB8927206 A GB 8927206A GB 8927206 A GB8927206 A GB 8927206A GB 2238541 A GB2238541 A GB 2238541A
Authority
GB
United Kingdom
Prior art keywords
organic materials
optical processing
compound
shg
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB8927206A
Other versions
GB2238541B (en
GB8927206D0 (en
Inventor
Michael Dunleavy
Norman Mark Ratcliffe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BAE Systems PLC
Original Assignee
British Aerospace PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by British Aerospace PLC filed Critical British Aerospace PLC
Priority to GB8927206A priority Critical patent/GB2238541B/en
Publication of GB8927206D0 publication Critical patent/GB8927206D0/en
Publication of GB2238541A publication Critical patent/GB2238541A/en
Application granted granted Critical
Publication of GB2238541B publication Critical patent/GB2238541B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A compound of the formula <IMAGE> wherein R is alkyl and X is a heteroatom, e.g. 2-(3-thienylethyl) 4-decyloxycinnamate, can be used for second harmonic generation.

Description

ORGANIC MATERIALS FOR USE IN OPTICAL PROCESSING Field of the Invention This invention relates to organic materials for use in optical processing.
Background of the Invention There has been considerable interest recently in organic materials for use in optical processing. One particular interest is the area of second harmonic generation (SHG), in which the frequency of coherent light is doubled during passage through a suitable substance. Thus, for example, infra-red light (1.06 ssm) from a Nd/YAG laser is converted to green light (0.53 ssm). Organic materials have several potential advantages over the inorganic materials most often used for SHG, including greater conversion efficiencies, and a high resistance to laser damage.
Although the literature contains many examples of organic materials capable of SHG activity, many suffer the disadvantage that they are absorbing in the green region of the spectrum. Such compounds generally have a amino-nitro donor-acceptor system, thought until now to be the best way of achieving strong SHG activity, and it is this system which can give rise to absorption bands in the green region.
Not all organic compounds are capable of SHG activity. It can be shown that the compound must have a non-centrosymmetric crystal structure.
Summary of the Invention Novel compounds which are not based on a amino-nitro donor-acceptor system are of formula I (see claim 1), wherein R is alkyl, e.g. of up to 14 or 20 C atoms, and usually of at least 4 C atoms, and X is a heteroatom such as O or S.
Description of the Invention The compound 2-(3-thienyl)ethyl 4-decyloxycinnamate (Ia = I : R = decyl, X = S), crystallises non-centrosymmetrically, is colourless, and exhibits strong SHG activity on irradiation with light from a Nd/YAG laser. In powder experiments, a visual comparison of the intensity of SHG for Ia and for 2-methyl 4-nitroaniline (a material often used as a standard in comparative studies) showed Ia to be much more active.
In addition, Ia appeared to be highly resistant to laser damage.
Compounds of formula I may be prepared by esterification of the RO-substituted-cinnamic acid with an ethanol-substituted heterocycle. The following Example illustrates this process.
Example To a solution of 2-(2-thienyl)ethanol (1.4 g, 11 mmol), 4-decyloxycinnamic acid (3.14 g, 10 mmol), and dicyclohexylcarbodiimide in chloroform (150-200 ml) (2.3 g, 11 mmol) was added 4-pyrrolopyridine (10 mg). The mixture was left to stir overnight. The mixture was filtered to remove the urea that had formed, the filtrate was washed with chloroform, and the filtrate and washings were combined and evaporated to yield the crude product.
Column chromatography (silica gel, packed and eluted with chloroform) furnished the product (Ia) which was recrystallised from methanol.

Claims (4)

1. A compound of the formula
wherein R is alkyl and X is a heteroatom.
2. 2-(3-Thienylethyl) 4-decyloxycinnamate.
3. A compound as claimed in claim 1 or claim 2, in single crystal form.
4. A method of second harmonic generation, which comprises directing coherent light onto a compound as claimed in any preceding claim.
GB8927206A 1989-12-01 1989-12-01 4-alkoxy-cinnamates for use in optical processing Expired - Fee Related GB2238541B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB8927206A GB2238541B (en) 1989-12-01 1989-12-01 4-alkoxy-cinnamates for use in optical processing

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB8927206A GB2238541B (en) 1989-12-01 1989-12-01 4-alkoxy-cinnamates for use in optical processing

Publications (3)

Publication Number Publication Date
GB8927206D0 GB8927206D0 (en) 1990-08-08
GB2238541A true GB2238541A (en) 1991-06-05
GB2238541B GB2238541B (en) 1993-02-17

Family

ID=10667269

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8927206A Expired - Fee Related GB2238541B (en) 1989-12-01 1989-12-01 4-alkoxy-cinnamates for use in optical processing

Country Status (1)

Country Link
GB (1) GB2238541B (en)

Also Published As

Publication number Publication date
GB2238541B (en) 1993-02-17
GB8927206D0 (en) 1990-08-08

Similar Documents

Publication Publication Date Title
US4251520A (en) Glucofuranose derivatives
RU94046169A (en) Heterocyclic compounds, method of their synthesis, method of separation of optical isomers, pharmacomposition, treatment method
ZA817696B (en) N-substituted omega-(2-oxo-4-imidazolin-1-yl)alcanoic acids,salts and esters thereof,process for producing the same and these active agents containing pharmaceutical compounds
PT70921A (en) Novel Indole derivatives of their production and their use as medicines
GB2238541A (en) Organic materials for use in optical processing
KR940011463A (en) Crystalline Carbapenem Derivatives
ATE83772T1 (en) ANTIHYPERCHOLESTEROLMIC 4,5-DIARYL-2 SUBSTITUTE THIOIMIDAZOLES.
US4461768A (en) Anti-inflammatory 1,2-benzothiazines
NO173501C (en) Analogous Procedures for the Preparation of Therapeutically Active Pyrazolo-Pyridine Compounds
US3573290A (en) Substituted cinnamic acids
JPS5663976A (en) Novel sulfonated compound containing lactone ring* its manufacture and application to manufacture of cyclopropane derivative
JPS5728046A (en) Preparation of 4-substituted indole
ES8307236A1 (en) Process for the preparation of a furan derivative.
ES483249A1 (en) Process for the preparation of dicyclopentylene [2,2&#39;-bis(4-alkyl-6-t-butylphenols)]
US3048596A (en) 3-cyano-[1, 3]-dithiolo-[4, 5-c]-isothiazole-delta5, alpha-malononitrile and process
US2976217A (en) Sunscreening agents
RU95108544A (en) Methods of synthesis of intermediate compounds of beta-methylcarbapenems, intermediate compounds
JPS5622763A (en) 25-hydroxy-24-oxovitamin d3, or its hydroxyl-protecting derivative and its preparation
US6093828A (en) Form of (E)-3-[6-[[(2,6-dichlorophenyl)-thio]methyl]-3-(2-phenylethoxy)-2-pyridi nyl]-2-propenoic acid
SU717038A1 (en) N-heteryloxaminates of 1-adamantylammonium possessing diurethic activity
Terao et al. 3-Aminoxanthene-9-one
Clapp et al. The Interconversion of 2-Substituted 2-Oxazolines and 2-Thiazolines
ES8401464A1 (en) Process for the preparation of 1-(4-chlorbenzoyl)-5-methoxy-2-methyl-3-indolacetoxy-acetic acid.
NO154496C (en) ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE NB QUARTERLY DERIVATIVES OF SANDWICIN AND ISOSANDWICIN.
PE99398A1 (en) NON-ULCEROGENIC ANALGESIC / ANTI-INFLAMMATORY DERIVATIVE OF CLONIXINE

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19981201