6.1 Literaturverzeichnis:
[1] Autorenkollektiv, Organikum, Deutscher Verlag der Wissenschaften, Berlin, 1976
[2] Fieser und Fieser, Organische Chemie, Verlag Chemie, Basel, 1982
[3] CD Römpp Chemielexikon, Thieme, Stuttgart, 1995
[4] March, Advanced organic chemistry, Wiley & Sons, New York, 1992
[5] Vollhardt, Schore, Organische Chemie, Wiley-VCH, Weinheim, 2000
[6] Kunze, Markus, Neue Fluoreszenzfarbstoffe mit Anthracen- und Fluoranthrengerüst, Dissertation, LMU München, 2004
[7] Behrens, Thomas, Darstellung von tricyclischen benzoiden Kohlenwasserstoffen mit elektronenziehenden Substituenten, Dissertation, Universität Hamburg, 1999
[8] Dufraisse, Charles , Etienne, Andre, Technique pour effectuer des reactions avec des corps peu solubles, College de France, Paris, 1947
[9] Okamoto et al., Process for producing 9,10-Diphenylanthracene, United States Patent, US 6,566,572 B2, 2003
[10] Sonogashira, Tohda, Hagihara, a convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Letters, 50, S. 4467–4470, 1975
[11] Thorand, Krause, improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides. Journal of organic chemistry, 1998, 63, S. 8551–8553
[12] Maryanoff, Reitz, Duhl-Emsweiler, Stereochemistry of the Wittig-reaction. Effect of nucleophilic groups in the phosphonium ylide. Journal of American Chemical Society, 1985, 107, S. 217–226
[13] Zhi, Yang, Lu, Wang, Synthesis and verification of 9,10-Diphenylanthracene. Chemical Educator, 2000, 5, S. 187–189
[14] Organic Syntheses, Coll. Vol. 1, S. 207 & Vol. 3, S. 41
6.2 Verwendete Chemikalien
1-Propanol, C3H8O (CAS: 71-23-8)
Gefahr
H225, H318, H336, P210, P240, P280, P305 + P351 + P338, P313, P403 + P233
2,4,6-Trichlorphenol, C6Cl3H3O (CAS: 88-06-2)
Achtung
H302, H315, H319, H351, H410, P273, P302 + P352, P305 + P351 + P338, P308 + P313
2,4-Dinitrophenol, C6H4N2O5 (CAS: 51-28-5)
Gefahr
H228, H301 + H311 + H331, H373, H400, P210, P260, P280, P301 + P330 + P331 + P310, P302 + P352 + P312, P304 + P340 + P311
2-Propanol, C3H8O (CAS: 67-63-0)
Gefahr
H225, H319, H336, P210, P240, P305 + P351 + P338, P403 + P233
9,10-Dibromanthracen, C14H8Br2 (CAS: 523-27-3)
Achtung
H410, P273, P501
9,9′-Bianthryl, C28H18 (CAS: 1055-23-8)
Acetonitril, C2H3N (CAS: 75-05-8)
Gefahr
H225, H302 + H312 + H332, H319, P210, P240, P302 + P352, P305 + P351 + P338, P403 + P233
Aluminium(III)-oxid, Al2O3 (CAS: 1344-28-1)
P260
Anthracen, C14H10 (CAS: 120-12-7)
Achtung
H315, H319, H335, H410, P261, P273, P305 + P351 + P338, P501
Anthracen-9-carbaldehyd, C15H10O (CAS: 642-31-9)
Anthrachinon, C14H8O2 (CAS: 84-65-1)
Achtung
H317, P280
Argon (gasförmig), Ar (CAS: 7440-37-1)
Achtung
H280, P403
Benzyltriphenylphosphoniumchlorid, C25H22ClP (CAS: 1100-88-5)
Gefahr
H300 + H330, H311, H315, H319, H335, H411, P260, P273, P301 + P310 + P330, P304 + P340 + P310, P403 + P233
Bis(2,4,6-trichlorphenyl)-oxalat, C14H4Cl6O4 (CAS: 1165-91-9)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
Bis(2,4-dinitrophenyl)-oxalat, C14H6N6O12 (CAS: 16536-30-4)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
Bis(triphenylphosphin)-palladium(II)-chlorid, [(C6H5)3P]2PdCl2 (CAS: 13965-03-2)
Achtung
H302, H315, H317, H319, P280, P302 + P352, P305 + P351 + P338
Brom, Br2 (CAS: 7726-95-6)
Gefahr
H330, H314, H400, P210, P273, P304 + P340, P305 + P351 + P338, P308 + P310, P403 + P233
Brombenzol, C6H5Br (CAS: 108-86-1)
Achtung
H226, H315, H411, P273, P210, P302 + P352
Calciumchlorid wasserfrei gepulvert, CaCl2 (CAS: 10043-52-4)
Achtung
H319 , P305 + P351 + P338
Calciumhydrid, CaH2 (CAS: 7789-78-8)
Gefahr
H260, P402 + P404
Dichlormethan, CH2Cl2 (CAS: 75-09-2)
Achtung
H315, H319, H335, H336, H351, H373, P302 + P352, P305 + P351 + P338, P314
Diethylether, C4H10O (CAS: 60-29-7)
Gefahr
H224, H302, H336, EUH019, EUH066, P210, P240, P403 + P235
Dimethylphthalat, C10H10O4 (CAS: 131-11-3)
Essigsäure 100 %, C2H4O2 (CAS: 64-19-7)
Gefahr
H226, H290, H314, P210, P280, P301 + P330 + P331, P305 + P351 + P338, P308 + P310
Essigsäureethylester, C4H8O2 (CAS: 141-78-6)
Gefahr
H225, H319, H336, EUH066, P210, P240, P305 + P351 + P338, P403 + P233
Iod, I2 (CAS: 7553-56-2)
Gefahr
H312 + H332, H315, H319, H335, H372, H400, P273, P302 + P352, P305 + P351 + P338, P314
Kaliumiodid, KI (CAS: 7681-11-0)
Kupfer(I)-iodid, CuI (CAS: 7681-65-4)
Achtung
H410, P260, P273
Lithium, Li (CAS: 7439-93-2)
Gefahr
H260, H314, EUH014, P280, P301 + P330 + P331, P305 + P351 + P338, P308 + P310, P370 + P378, P402 + P404
Magnesium Späne, Mg (CAS: 7439-95-4)
Gefahr
H228, H252, H261, P210, P370 + P378, P402 + P404
Magnesiumsulfat wasserfrei, MgSO4 (CAS: 7487-88-9)
N,N-Dimethylformamid, C3H7NO (CAS: 68-12-2)
Gefahr
H360D, H226, H312 + H332, H319 , P201, P210, P302 + P352, P305 + P351 + P338, P308 + P313
n-Butyllithium Lösung 10.0 M in Hexan, CH3(CH2)3Li (CAS: 109-72-8)
Gefahr
H225, H250, H261, H304, H314, H336, H361f, H373, H411, EUH014, P210, P222, P231 + P232, P261, P422
Natriumbenzoat, C7H5NaO2 (CAS: 532-32-1)
Natriumphosphinat-Monohydrat, NaH2PO2· H2O (CAS: 10039-56-2)
Natriumsalicylat, C7H5NaO3 (CAS: 54-21-7)
Achtung
H302, H319 , P305 + P351 + P338
Natriumsulfat wasserfrei, Na2SO4 (CAS: 7757-82-6)
Natronkalk
Gefahr
H290, H318, H335, P280, P305 + P351 + P338 + P313
Natronlauge 50 %, NaOH (CAS: 1310-73-2)
Gefahr
H290, H314, P280, P301 + P330 + P331, P305 + P351 + P338, P308 + P310
Nickel(II)-acetylacetonat, C10H14NiO4 (CAS: 3264-82-2)
Achtung
H302, H317, P262, P280, P302 + P352
Oxalylchlorid, C2Cl2O2 (CAS: 79-37-8)
Gefahr
H260, H314, H331, H335, EUH014, EUH029, P280, P301 + P330 + P331, P304 + P340, P305 + P351 + P338, P308 + P310, P402 + P404
Petrolether Siedebereich 50–70 °C, (CAS: 8032-32-4)
Gefahr
H225, H304, H315, H336, H361f, H373, H411, P201, P210, P301 + P310 + P331, P370 + P378, P501
Phenylacetylen, C8H6 (CAS: 536-74-3)
Gefahr
H226, H304, H315, H319, P210, P301 + P310 + P331, P302 + P352, P305 + P351 + P338
Phosphor(V)-oxid, P4O10 (CAS: 1314-56-3)
Gefahr
H314, EUH014, P260, P280, P303 + P361 + P353, P304 + P340 + P310, P305 + P351 + P338
Pyrogallol, C6H6O3 (CAS: 87-66-1)
Achtung
H302 + H312 + H332, H341, H412, P273, P280, P302 + P352, P308 + P313
Salzsäure 37 %, HCl (CAS: 7647-01-0)
Gefahr
H290, H314, H335, P280, P301 + P330 + P331, P305 + P351 + P338, P308 + P310
Salzsäure c(HCl) = 2 mol/L, HCl (CAS: 7647-01-0)
Achtung
H290
Schwefelkohlenstoff, CS2 (CAS: 75-15-0)
Gefahr
H225, H315, H319, H361fd, H372, P210, P233, P240, P280, P302 + P352, P305 + P351 + P338, P308 + P313, P403 + P233
Stickstoff (gasförmig), N2 (CAS: 7727-37-9)
Achtung
H280, P403
Stickstoff (tiefgekühlt, flüssig), N2 (CAS: 7727-37-9)
Achtung
H281, P282, P336 + P315, P403
tert-Butanol, C4H10O (CAS: 75-65-0)
Gefahr
H225, H319, H332, H335, P210, P305 + P351 + P338, P403 + P235
Tetrachlorkohlenstoff, CCl4 (CAS: 56-23-5)
Gefahr
H301 + H311 + H331, H317, H351, H372, H412, H420, P261, P273, P280, P301 + P310 + P330, P403 + P233, P502
Tetrahydrofuran, C4H8O (CAS: 109-99-9)
Gefahr
H225, H319, H335, H351, EUH019, P210, P240, P305 + P351 + P338, P308 + P313, P403 + P233
Toluol, C7H8 (CAS: 108-88-3)
Gefahr
H225, H304, H315, H336, H361d, H373, P210, P240, P301 + P330 + P331, P302 + P352, P308 + P313, P314, P403 + P233
Triethylamin, C6H15N (CAS: 121-44-8)
Gefahr
H225, H302 + H312 + H332, H314, H335, P210, P233, P240, P280, P301 + P330 + P331, P302 + P352, P304 + P340, P305 + P351 + P338,
P308 + P313, P403 + P235
Trimethylphosphat, (CH3)3PO4 (CAS: 512-56-1)
Gefahr
H351, H340, H302, H315, H319, P201, P280, P302 + P352, P305 + P351 + P338, P308 + P313
Zinn gekörnt, Sn (CAS: 7440-31-5)
6.3 Geeignete Luminophore
1,4-Bis(2-methylstyryl)-benzol, C24H22 (CAS: 13280-61-0)
Achtung
H302, H319, H413, P305 + P351 + P338
1,8-Dichlor-9,10-bis(phenylethinyl)-anthracen, C30H16Cl2 (CAS: 51749-83-8)
Achtung
H302, H312, H315, H319, H332, H335, H351, P261, P280, P305 + P351 + P338
1-Chlor-9,10-bis(phenylethinyl)-anthracen, C30H17Cl (CAS: 41105-35-5)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
1-Chlor-9,10-diphenylanthracen, C26H17Cl (CAS: 43217-27-2)
Achtung
H315, H319, H335, P280
2-Chlor-9,10-bis(phenylethinyl)-anthracen, C30H17Cl (CAS: 41105-36-6)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
2-Chlor-9,10-diphenylanthracen, C26H17Cl (CAS: 43217-28-3)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
5,12-Bis(phenylethinyl)-naphthacen, C34H20 (CAS: 18826-29-4)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
9,9′-Bianthryl, C28H18 (CAS: 1055-23-8)
9,10-Bis(phenylethinyl)-anthracen, C30H18 (CAS: 10075-85-1)
Achtung
H315, H319, H335, P261, P305 + P351 + P338
9,10-Di-n-butylanthracen, C22H26 (CAS: 1624-34-6)
(Gefahr)
Unbekannte Eigenschaften. Es liegt kein Sicherheitsdatenblatt vor.
9,10-Diphenyl-9,10-dihydro-anthracen, C26H20 (CAS: 803-58-7)
(Gefahr)
Unbekannte Eigenschaften. Es liegt kein Sicherheitsdatenblatt vor.
9,10-Diphenylanthracen, C26H18 (CAS: 1499-10-1)
10,10′-Diphenyl-9,9′-bianthryl, C40H26 (CAS: 23102-67-2)
(Gefahr)
Unbekannte Eigenschaften. Es liegt kein Sicherheitsdatenblatt vor.
13,13′-Dibenzanthronyl, C34H18O2 (CAS: 116-96-1)
Achtung
H302, H319, H413, P305 + P351 + P338
Cresylviolettacetat, C18H15N2O3 (CAS: 10510-54-0)
Cumarin 6, C20H18N2O2S (CAS: 38215-36-0)
Eosin B, C20H6Br2N2Na2O9 (CAS: 548-24-3)
Fluorescein Natriumsalz, C20H10Na2O5 (CAS: 518-47-8)
Isoviolanthron, C34H16O2 (CAS: 128-64-3)
KF-856, C72H58N2O8 (CAS: 123174-58-3)
Luciferin, C11H8N2O3S2 (CAS: 2591-17-5)
Luminogen F violett, C12H7NO2 (CAS: 81-83-4)
Achtung
H302
Magnesiumphthalocyanin, C32H16MgN8 (CAS: 1661-03-6)
N,N′-Dimethyl-9,9′-biacridiniumdinitrat (Lucigenin), C28H22N4O6 (CAS: 2315-97-1)
Perylen, C20H12 (CAS: 198-55-0)
Phenanthrenchinon, C14H8O2 (CAS: 84-11-7)
Achtung
H319, H400, P262, P273, P305 + P351 + P338
Rhodamin 6G, C28H31N2O3Cl (CAS: 989-38-8)
Achtung
H302
Rhodamin 110, C20H14N2O3 · HCl (CAS: 13558-31-1)
Rhodamin B, C28H31ClN2O3 (CAS: 81-88-9)
Gefahr
H318, H412, P260, P273, P280, P305 + P351 + P338
Rubren, C42H28 (CAS: 517-51-1)
Tetracen, C18H12 (CAS: 92-24-0)
trans-9-(2-phenylethenyl)-anthracen, C22H16 (CAS: 42196-97-4)
Achtung
H315, H319, H335, P280
Violanthren, C34H20 (CAS: 81-31-2)
(Gefahr)
Unbekannte Eigenschaften. Es liegt kein Sicherheitsdatenblatt vor.
Violanthron, C34H16O2 (CAS: 116-71-2)
Achtung
H302, H315, H319, H335, P261, P264, P280, P301 + P312, P302 + P352, P304 + P340