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US6500363: Classes of high linear and nonlinear response compounds

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Filing Information

Inventor(s) James T. Spencer · Damian G. Allis ·
Assignee(s) Syracuse University ·
Attorney/Agent(s) Wall Marjama & Bilinski LLP ·
Primary Examiner Robert Dawson ·
Assistant Examiner Kuo Liang Peng ·
Application Number US9602424
Filing date 06/23/2000
Issue date 12/31/2002
Predicted expiration date 09/19/2020
Patent term adjustment 88
U.S. Classifications 252/582  · 585/24  · 568/4  · 568/3  · 556/8  · 252/587  · 252/588  · 252/589  · 385/5  ·
International Classifications --
Kind CodeB1
International Classifications 385 5 · 556 8 · 568 4 · 568 3 · 585 24 · 252582 · 252587 · 252588 · 252589 ·
Related U.S. Application DataThis application claims the benefit of provisional application Serial No. 60/141,343, filed Jun. 28, 1999.
20 Claims, 7 Drawings


Abstract

A class of molecules suitable for linear and nonlinear optical applications which include charged aromatic groups which function as electronic donors and acceptors connected through polyhedral and -organic and inorganic groups. The polyhedral and -organic and inorganic groups function as structural and electronic bridges for the charged donors and acceptors.

Independent Claims | See all claims (20)

  1. 1. A compound suitable for linear and nonlinear optical applications which comprises charged aromatic groups which function as electronic donors and acceptors connected through polyhedral and/or -aromatic and inorganic groups.
  2. 3. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H6−1)B12H10(R)2− where R is any one of C5H4−1; C5Me4−1; C5Et4−1; C5(C6H5−1)4; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; or C5H2Ph2−1.
  3. 4. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H6)C4B20H20(R) where R is C5H4−1; C5Me4−1; C5Et4−1; C5(C6H5−1)4; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; or C5H2Ph2−1.
  4. 5. A compound suitable for linear and non-linear optical applications having the general formula: (C7H61)B10H12(R) or (C7H61)B10H8(R)2− where R is C5H4−1; C5Me4−1; C5Et4−1; (C5(C6H5)4)−1; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; C5H2Ph2−1 or C5Me4−1.
  5. 6. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H61)B27H28(R) where R is C5H4−1; C5Me4−1; C5Et4−1; (C5(C6H5)4)−1; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; C5H2Ph2−1 or C5Me4−1.
  6. 7. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H61)R(R′) where R is hydrindacene and R′ is C5H4−1; C5Me4−1; C5Et4−1; (C5(C6H5)4)−1; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; or C5H2Ph2−1.
  7. 8. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H61)C2B10H10(R) where R is any one of C5H4−1; C5Me4−1; C5Et4−1C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; C5(Ph)4−1; and C2B10H11.
  8. 9. A compound suitable for linear and nonlinear optical applications having the general formula: (R)B12H10−2—C2B10H10(R′) where R is C7H61 and R′ is C5H4−1, C5Me4−1, or H; or where R is C5H4−1, C5Me4−1, or H and R′ is C7H61.
  9. 10. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H61)B18H20(R) where R is any one of C5H4−1 and C5Me4−1.
  10. 11. A compound suitable for linear and nonlinear optical applications having the general formula: (C3R′2)B12H10(R)2− where R is C5H4−1 and R′ is H; or where R is C5Me4−1 and R′ is H.
  11. 12. A compound suitable for linear and nonlinear optical applications having the general formula: 1,4-(NH2)C2B10H10(NO2).
  12. 13. A compound suitable for linear and nonlinear optical applications having the general formula: (C7H6)R(R′)n (where n is 0 or −1) where R is based on either unsubstituted or substituted variant species of cyclopropa4,5benzocyclobutene; benzo1,2:4,5dicyclobutene; tetrahydrocyclopropfindene; 4,5-cyclopentenobenzocyclobutene; octahydrohydrindacene; tetrahydrocyclopropabnaphthalene; hexahydrocyclobutanaphthalene; tetrahydrobenzindane; and octahydroanthracene and R′ is any one of C5H4−1; C5Me4−1; C5Et4−1; C5Ph4−1; C5H2Ph2−1; C5H2Me2−1; C5H3Me−1; C2B10H11; CH3; C5(CN)2Me2−1; C5(CN)3Me−1; C5(CN)2Ph2−1; BC5H5−1; C6Me3H2; NH2; and NMe2.
  13. 14. A compound which exhibits enhanced NLO properties which employs aromatic units which serve as donors and acceptors which are connected through polyhedral and/or -electron delocalized bridging groups, wherein said donors, acceptors and bridging groups comprise: (a) donors selected from the group consisting of C5H4−1; C4H3−2; BC5H5−1; B10H9−2; B12H11−2; CB9H9−1; CB11H11−1; C2B4H5; C2B8H9; C2B10H11; B10H13; and B5H8; (b) acceptors selected from the group consisting of C7H61; C3H21; NC5H51; SC5H41; FeCp2; Fe(CO)n (where n1, 2, 3, 4); FeCp(CO)2; B5H4−2; B6H52−; B12H122−; C2B4H5; C2B8H9; C2B10H11; B10H13; B5H8; and (c) bridge groups selected from the bridge groups in borane polyhedral compounds, carborane polyhedral compounds and -aromatic compounds as shown in I through IX: wherein A is an acceptor, and D is a donor.

References Cited

U.S. Patent Documents

Document NumberAssigneesInventorsIssue/Pub Date
US4288585 NASA Allock et al. Sep 1981
US4818898 E. I. Du Pont de Nemours and Company Anderson et al. Apr 1989
US4859876* American Telephone and Telegraph Company; AT&T Bell Laboratories Dirk et al. Aug 1989
US4962979 E. I. Du Pont de Nemours and Company Anderson et al. Oct 1990
US5844052 The United States of America as represented by the Secretary of the Navy Keller et al. Dec 1998

Foreign Patent Documents

Document NumberAssigneesInventorsIssue/Pub Date
JP01291223IDEMITSU KOSAN CO LTDOct 1989
* cited by examiner

Other Publications

Abe et al., Heterocyclic Betaines Exhibiting Extremely Large First Hyperpolarizability: Ab Initio and INDO/S Calculation, Journal of Amenican Chemical Society, vol. 118, 4707-4706 (1996).*
Harmon et al. Journal of the American Chemical Society, 89, 5309-5311 (1967).*
Yamaguchi et al, Bulletin of The Chemical Society of Japan, vol. 48(4), 1325-1326 (1975).*
Takahashi et al., Tetrahedron Letters, No. 50, 4655-46-58 (1976).*
Lee, S-G. et al., Synthesis of (ferrocenyl-indenyl) cyclopentadienyliron compounds with and without a bridging group via a CpFe transfer reaction. Inorganica Chimica Acta, Mar. 15, 1999, vol. 286, No. 2, pp. 215-220, especially pp. 218-219.

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