Laser dye structures and synonyms Joel M. Kauffman Laser dyes are organic chemicals whose systematic names are lengthy and confusing. Other names-some come into everyday use, but there is no consistency, and sometimes research workjargon, some trade-have This ers will have dyes from different suppliers that are identical in structure although different in name. paper tabulates laser dyes by a characteristic identification number. Laser dyes are organic chemicals whose systematic names are lengthy and confusing. Jargon names have come into use which do not indicate the structure of the dyes. Commercial suppliers of laser dyes have different systems of trade names, and the Naval Weapons Center developed a system of its own for bicyclic dyes. Structures for a given dye in the literature often dis- agree, and researchers may be unaware that they have dyes from different suppliers which are identical in structure despite a difference in name. Physicists are generally unaware that there is an easy computer-based method to search the literature for a given laser dye by a characteristic identification number. Table I shows the structural formulas of 30 laser dyes of current interest that have two or more popular names. The dyes are numbered 1-30 for easy reference, but they are arranged in order of increasing untuned peak laser output wavelength. While this wavelength can vary greatly depending on dye concentration, cell dimensions, and solvent, the wavelengths selected for Table I place the dyes in the correct relative order for similar conditions. The structural formulas are drawn in similar orientations so that related dyes may be compared easily. Note that dyes 15 and 16 differ by just one methylene (CH 2 ) group; this is the reason for inclusion of dye 16, which has only one jargons name. An alpha- betic/numeric index is provided in Table II to aid in locating dyes in Table I. Chemical Abstracts indexes many applied physics journals citing performance of laser dyes as well as The author is with Philadelphia College of Pharmacy & Science, 43rd Street & Kingsessing Mall, Philadelphia, Pennsylvania 19104. Received 25 June 1980. 0003-6935/80/203431-05$00.50. © 1980 Optical Society of America. chemistry journals that may describe syntheses of the dyes. The Chemical Abstracts Registry Number, when available, has been included in Table I for each dye. This number may be used to search the literature for citations past or future to each dye in Table I with the qualifier laser by accessing one of the appropriate computer-based chemical dictionaries. Examples are Chemdex (System Development Corp.), Chemname and Chemline (Lockheed Missiles & Space Corp.), (National Library of Medicine).'9 15 October 1980 / Vol. 19, No. 20 / APPLIED OPTICS 3431 TableI. Structures andSynonyms of LaserDyes Dye Laser no. Xa 1 386 nm Structural formula Common names of dye ~, of dyeb /= CH3ICH1)1CHCHO0i 4\ ,,\ C.C.(~}H. (H 2) 3CH3 "C'H \" \ I \\ I 2CH3 BIBUQ (EM Labs) - -.Filot 386 (N) Chem. Abst. reg. no.c Literature references 18434-08-7 1,2 26078-25-1 3-6,18 BBQ (X) CH3 2 446 C 2 HsC3(A0 CH Coumarin 2 (K) Coumarin 450 (X) H 3 H 4 BMU CH3 Beta-methylumbelliferone 456 CH3 h C2 H5 C2 H- 5 466 C2Hs 7,18 91-44-1 3-6,8,11,18 Coumarin 4 (K) Pilot 447 (N) OJg$1O 460 90-33-5 J( o Coumarin 1 (K) MDAC Pilot 449 (N) 7DEA4MC (W) Coumarin 460 (X) C1H (W) LD 466 (X) 57597-38-3 3,5,9 Q6F (W) LD 473 (X) 58721-74-7 3,5,9,18 Coumarin 102 (K) Coumarin 480 (X) 41267-76-9 3-6,8-11,18 Coumarin 35 (K) Pilot 481 (N) C1F (W) Coumarin 481 (X) 41934-47-8 4,5,11,12 Coumarin 151 (K) C3F (W) Coumarin 490 (X) 53518-15-3 4-6,11,18 C6H (W) LD 490 (X) 58336-35-9 3,9,18 Coumarin 307 (K) Coumarin 503 (X) 55804-70-1 4,6,18 Coumarin 314 (K) Coumarin 504 (X) 55804-66-5 4,6,8,18 C2 H5 6 CH n-CH3 473 CF3 3 H3 7 480 8 481 CH3 CF3 C2H5j j C2 H5 9 CF3 490 H2 NJI 10 490 11 503 12 506 O CF3 3432 C 2 HsJ OCH5 APPLIED OPTICS/ Vol. 19, No. 20 / 15 October 1980 Table 1. Structuresand Synonymsof Laser Dyes (continued) Dye Laser Structural formula no. Xa of dye 13 515 nm N Common names Chem. Abst. Literature of dyeb reg. no.c references Coumarin 30 (K) Coumarin 515 (X) 41044-12-6 3,5,6,9,10,18 Coumarin 152 (K) C2F (W) Coumarin 485 (X) 53518-14-2 4-6,11,18 C8F (W) Coumarin 522 (X) 53518-19-7 5,9,11,18 Coumarin 355 (K) C15H14 F3 NO2 C Coumarin 7 (K) Coumarin 535 (X) 27425-55-4 6,18 Coumarin 6 (K) Coumarin 540 (X) 38215-36-0 3-6,8,10,18 Coumarin 153 (K) Pilot 495 (N) C6F (W) Coumarin 540A (X) 53518-18-6 4-6,8,9,11,12,18 Rhodamine 110 (K) Rhodamine 560 (X) 13558-31-1 8,23 C2 H(S CF3 14 519 CH3 ' CF3 15 522 CH3 CF3 16 522 4 C2H5 17 535 C 2 H, H I C2 H5 N9Z 18 540 C2 0 %H~JoI7Io C2H5 19 543 20 570 H N2 H 2 0 CC02H 21 590 H5 CH r- CNHHC COH CC +,C2Hs C2H5 22 H 590 CO c 2 C 2 H5 - C 2 C104- C. I. Basic Red 1 Rhodamine 5GDNd (D) Rhodamine 6G (D,K) Rhodamine 6GDN (D) Rhodamine 69DN (D) Pilot 559 (N) Rhodamine 590 Chloride (X) 989-38-8 Rhodamine 6G Perchlorate (K) Pilot 559P (N) Rhodamine 590 Perchlorate (X) 13161-28-9 8,11,13 8,22 15 October 1980 / Vol. 19, No. 20 / APPLIED OPTICS 3433 Table 1. Structuresand Synonymsof Laser Dyes (continued) Dye Laser Structural formula no. \a of dye 23 610 nm 1 C2 H5 11 2 H5 2H -C 24 Common names Chem. Abst. Literature of dyeb reg. no. C references C. I. Basic Violet 10 C. I. Food Red 15 Rhodamine B (D,K) Pilot 578 (N) Rhodamine 610 (X) cl- 620 !HS C. I. Acid Red 52 81-88-9 8,13,14 2609-88-3 13,14 41175-43-3 8,15 60311-02-6 20,21 41830-80-2 8,16 53340-16-2 8,16 Oxazine 170 Perchlorate (K) Oxazine 720 (X) 62669-60-7 6,8 Oxazine 1 24796-94-9 8,24 Kiton Red S Kiton Red 620 (X) Sulforhodamine B (K) Xylene Red B 25 640 Rhodamine 101 (K) Rhodamine 640 Perchloratee (X) 26 648 Sulforhodamine 101 (K) Sulforhodamine 640 (X) 27 670 C 25 H2N°H2 Cresyl Violet 670 (X) Cresyl Violet C N0 28 690 c Oy%NN > H2 Nile Blue 690 (X) Nile Blue A K J L0 Nt H-f -C( C2H5% 29 Perchlorate (K) + Perchlorate (K) Pilot 730f (N) C2H5 720 C H aN MCH Cl04- 30 725 C 2 H+C2 C2HS"' '-II H 5 C2 H5 Cloz Perchlorate (K) Oxazine 725 (X) Pilot 740 (N) The untuned laser output wavelength maximum is given, usually in ethanol. Abbreviations: D = DuPont; K = Eastman Kodak; N = New England Nuclear; W = Naval Weapons Center; C.I. = Colour Index1 7; X Exciton Chemical Co. a b = c Where the Chemical Abstracts registry number was not available, the empirical formula is given. d The dye known as Rhodamine 6G is a mixture whose major component is the structure shown, available from Du Pont as Rhodamine GDN Extra. The chloride portion of the structure is actually included in the name Rhodamine 6G (or GDN Extra), thus the common name Rhodamine 6G Perchlorate is a misnomer. e Rhodamine 101 is actually a chloride as shown. Rhodamine 640 has a perchlorate in place of a chloride. Its registry number is not available; the empirical formula is C 3 2 H31ClN207 . f Pilot 730 is actually the chloride, registry number 2381-85-3, also called C.I. Basic Blue 12. 3434 APPLIED OPTICS/ Vol. 19, No. 20 / 15 October 1980 Index TableII. Alphabetic/Numeric Dye no. Name 1 2 1 2 5 8 14 9 19 10 15 24 21 23 23 4 2 3 18 17 13 8 7 9 14 19 11 12 BBQ Beta-methylumbelliferone BIBUQ BMU ClH ClF C2F C3F C6F C6H C8F C.I. Acid Red 52 C.I. Basic Red 1 C.I. Basic Violet 10 C.I. Food Red 15 Coumarin 1 Coumarin 2 Coumarin 4 Coumarin 6 Coumarin 7 Coumarin 30 Coumarin 35 Coumarin 102 Coumarin 151 Coumarin 152 Coumarin 153 Coumarin 307 Coumarin 314 Dye no. Name 16 2 4 7 8 14 9 11 12 13 15 17 18 19 27 27 4 24 24 5 6 10 4 28 28 30 29 29 Coumarin 355 Coumarin 450 Coumarin 460 Coumarin 480 Coumarin 481 Coumarin 485 Coumarin 490 Coumarin 503 Coumarin 504 Coumarin 515 Coumarin 522 Coumarin 535 Coumarin 540 Coumarin 540A Cresyl Violet 670 Cresyl Violet Perchlo. 7DEA4MC Kiton Red S Kiton Red 620 LD 466 LD 473 LD 490 MDAC Nile Blue 690 Nile Blue A Perchlo. Oxazine 1 Perchlo. Oxazine 170 Perchlo. Oxazine 720 Name . Oxazine 725 Pilot 386 Pilot 447 Pilot 449 Pilot 481 Pilot 495 Pilot 559 Pilot 559P Pilot 578 Pilot 730 Pilot 740 Q6F Rhodamine 5GDN Rhodamine 6G Rhodamine 6G Perchlo. Rhodamine Rhodamine Rhodamine Rhodamine Rhodamine Rhodamine 6GDN 69DN 101 110 560 590 Chlo. Rhodamine 590 Perchlo. Rhodamine 610 Rhodamine 640 Perchlo. Rhodamine B Sulforhodamine Sulforhodamine Sulforhodamine Xylene Red B 101 640 B Dye no. 30 1 3 4 8 19 21 22 23 28 30 6 21 21 22 21 21 25 20 20 21 22 23 25 23 26 26 24 24 The encouragement of S. E. Neister of Phase-R Corporation and of R. W. Terhune of Optics Letters, and the help given by R. Steppel of Exciton Chemical Corporation and by P. Campbell and P. Doherty of this College are gratefully recognized. References 12. J. A. Halstead and R. R. Reeves, Opt. Commun. 27, 273 (1978). 1. H. Daussy, R. Dumanchin, and 0. de Witte, Appl. Opt. 17, 451 (1978). 2. K. L. Matheson and J. M. Thorne, Appl. Phys. Lett. 33, 803 (1978). 3. E. J. Schimitschek, J. A. Trias, P. R. Hammond, R. A. Henry, and R. L. Atkins, Opt. Commun. 16, 313 (1976). 4. G. A. Reynolds and K. H. Drexhage, Opt. Commun. 13, 222 (1975). 5. A. N. Fletcher, Appl. Phys. 14, 295 (1977). 6. K. H. Drexhage and G. A. Reynolds, IEEE J. Quantum Electron. QE-l0, 695 (1974). 7. K. H. Drexhage, G. R. Erikson, G. H. Hawks, and G. A. Reynolds, Opt. Commun. 15, 399 (1975). 8. K. H. Drexhage, J. Res. Natl. Bur. Stand. Sect. A: 80, 421 (1976). 9. E. A. Stappaerts, Appl. Opt. 16, 3079 (1977). 10. C. B. Collins, K. N. Taylor, and F. W. Lee, Opt. Commun. 26,101 (1978). 11. E. J. Schimitschek, J. A. Trias, P. R. Hammond, and R. L. Atkins, Opt. Commun. 11, 352 (1974). (1979). 14. P. R. Hammond, Opt. Commun. 29, 331 (1979). 15. G. A. Reynolds, U.S. Patent 4,005,092 (25 Jan. 77); Chem. Abstracts 86, 157047 (1977). 16. R. Harris and S. Stevens, Technical Report Air Force Material Laboratory, AFML-TR-74-37, Part 2 (1975). 13. P. R. Hammond, IEEE J. Quantum Electron. QE-15, 624 17. Colour Index, 3rd edition (Society of Dyers & Colourists and 18. 19. 20. 21. 22. 23. 24. American Association of Textile Chemists & Colorists, P.O. Box 12215, Research Triangle Park, N.C. 27709, 1971-75). A. N. Fletcher and D. E. Bliss, Appl. Phys. 16, 289 (1978). J. Kasperko, Database 9/79, 24. R. Koenig, G. Minkwitz, and B. Christov, Opt. Commun. 32,301 (1980). C. D. Decker, Appl. Phys. Lett. 33, 323 (1978). S. J. Sheldrake and H. H. L. Wang, U.S. Patent 4,139,342 (13 Feb. 79); Chem. Abstracts 90, 144163 (1979). R. E. Stickel, Jr., S. Blit, G. F. Hildebrandt, E. D. Dahl, F. B. Dunning, and F. K. Tittel, Appl. Opt. 17, 2270 (1978). S. Blit, E. G. Weaver, T. A. Rabson, and F. K. Tittel, Appl. Opt. 17,721 (1978). 15 October 1980 / Vol. 19, No. 20 / APPLIED OPTICS 3435
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