Second harmonic Generation with achiral, Straight-chain carbamic acid derivatives

• US 5,059,002 A
• Filed: 12/21/1989
• Issued: 10/22/1991
• Est. Priority Date: 12/21/1989
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Francis, Cecil V., Tiers, George V. D.
• Primary Examiner(s): Mintel, William
• Assistant Examiner(s): POTTER, ROY KARL
• Application Number:
  US07/454,755
• Time in Patent Office: 670 Days
• Field of Search: 350/354, 350/96.34, 350/353, 307/425, 307/427, 252/582, 252/600, 372/22
• US Class Current: 359/328
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 275/30 being further substituted by halogen atoms, or by nitro or nitroso groups

Abstract

Devices for and method of generating coherent second harmonic light radiation. The devices comprise a laser source of coherent light radiation at a fixed fundamental frequency, an acentrically crystalline, achiral, straight-chain N-nitrophenyl carbamyl compound, means for directing the output radiation of the laser onto the acentrically crystalline, achiral, straight-chain N-nitrophenyl carbamyl compound, and output means for utilizing the second harmonic frequency. N-nitrophenyl carbamyl compounds, and acentric crystals thereof that are capable of being used in the aforementioned devices and method, are also described herein.

Claims

1. A second harmonic generator comprising a laser source of coherent light radiation at a fixed fundamental frequency, an acentrically crystalline, achiral, organic compound, means for directing the output radiation of the laser onto said compound, and output means for utilizing the second harmonic frequency, said compound being a straight-chain N-nitrophenyl carbamyl compound crystallized in a non-centrosymmetric configuration, said crystalline compound being transparent to radiation at said fixed fundamental frequency and said second harmonic frequency, and said crystalline compound being a derivative of an N-nitrophenyl carbamic acid such that the straight chain is linked to the carbamyl carbon atom by an oxygen atom or nitrogen atom.

2. The second harmonic generator of claim 1, wherein said compound is selected from a group represented by the formulae:

space="preserve" listing-type="equation">R.sup.1 HNCONHR.sup.2 (I)

and

space="preserve" listing-type="equation">R.sup.1 HNCO.sub.2 R.sup.2 (II)

where R¹ represents one member of a group consisting of a nitrophenyl and substituted nitrophenyl group, and R² represents a group having two to twenty-two catenated methylene groups terminated by R³, where R³ represents a member selected from the group consisting of hydrogen, halogen, unsubstituted ethinyl group, substituted ethinyl group, unsubstituted vinyl group, substituted vinyl group, hydroxy group, alkoxy group, aryloxy group, acyloxy group, alkanesulfonyloxy group, arenesulfonyloxy group, alkanesulfonyl group, arenesulfonyl group, aryloxysulfonyl group, alkylthio group, arylthio group, cyano group, unsubstituted carbonyl, substituted carbonyl group, unsubstituted aryl group, substituted aryl group, unsubstituted amino group, substituted amino group, acyl amino group, and heterocyclic group.

3. The second harmonic generator of claim 1, wherein said compound is selected from a group represented by the formulae:

space="preserve" listing-type="equation">R.sup.1 HNCONHR.sup.2 (I)

and

space="preserve" listing-type="equation">R.sup.1 HNCO.sub.2 R.sup.2 (II)

where R¹ represents one member of a group consisting of an unsubstituted nitrophenyl group and a substituted nitrophenyl group, and R² represents a polymethylene group having two to twenty-two catenated methylene groups terminated by one member of a group consisting of a hydrogen atom, a halogen atom, an unsubstituted vinyl group, a substituted vinyl group, an unsubstituted ethinyl group, a substituted ethinyl group, an unsubstituted aryl group, a substituted aryl group, a hydroxy group, an ether group, an ester group, a thioether group, and a thiolester group.

4. The second harmonic generator of claim 1, wherein said laser is a Nd-YAG laser.

5. The second harmonic generator of claim 1, wherein said laser is a solid-state laser.

6. A process for converting a fixed fundamental frequency of coherent laser light into a second harmonic frequency which comprises passing said laser light through a nonlinear optical element comprising an acentrically crystalline, achiral, organic compound, said compound being a straight-chain N-nitrophenyl carbamyl compound crystallized in a non-centrosymmetric configuration, said crystalline compound being transparent to said fixed fundamental frequency and to said second harmonic frequency, and said crystalline compound being a derivative of an N-nitrophenyl carbamic acid such that the straight chain is linked to the carbamyl carbon atom by one member of a group consisting of an oxygen atom and nitrogen atom.

7. The process of claim 6, wherein said acentrically crystalline compound is selected from a group represented by the formulae:

space="preserve" listing-type="equation">R.sup.1 HNCONHR.sup.2 (I)

and

space="preserve" listing-type="equation">R.sup.1 HNCO.sub.2 R.sup.2 (II)

where R¹ represents one member of a group consisting of a nitrophenyl and substituted nitrophenyl group, and R² represents a group having two to twenty-two catenated methylene groups terminated by R³, where R³ represents a member selected from the group consisting of hydrogen, halogen, unsubstituted ethinyl group, substituted ethinyl group, unsubstituted vinyl group, substituted vinyl group, hydroxy group, alkoxy group, aryloxy group, acyloxy group, alkanesulfonyloxy group, arenesulfonyloxy group, alkanesulfonyl group, arenesulfonyl group, aryloxysulfonyl group, alkylthio group, arylthio group, cyano group, unsubstituted carbonyl, substituted carbonyl group, unsubstituted aryl group, substituted aryl group, unsubstituted amino group, substituted amino group, acyl amino group, and heterocyclic group.

8. The process of claim 6, wherein said acentrically crystalline compound is selected from a group of represented by the formulae:

space="preserve" listing-type="equation">R.sup.1 HNCONHR.sup.2 (I)

and

space="preserve" listing-type="equation">R.sup.1 HNCO.sub.2 R.sup.2 (II)

where R¹ represents one member of a group consisting of an unsubstituted nitrophenyl group and a substituted nitrophenyl group, and R² represents a polymethylene group having two to twenty-two catenated carbon atoms terminated by a hydrogen atom, a halogen atom, an unsubstituted vinyl group, a substituted vinyl group, an unsubstituted ethinyl group, a substituted ethinyl group, an unsubstituted aryl group, a substituted aryl group, a hydroxy group, an ether group, an ester group, a thioether group, and a thiolester group.