TA: HSIEN-PO CHIU Nov 13 & 15, 2007 Synthesis and chemiluminescence of luminol Principle 1. Reactions for synthesizing luminol COOH COOH NO 2 + NH 2 NH 2 (heat) NH NH NO 2 O O Na 2 S 2 O 4 NH NH NH 2 O O 3-nitrophthalic acid MW 211.13 hydrazine luminol (3-aminophthalhydrazide) MW 177.16 sodium dithionite sodium hydrosulfite triethylene glycol boiling point 285 o C- 2H 2 O S 2 O 4 2-+ 4 OH-2 SO 3 2-+ 2 H 2 O + 2 e-E=1.12V 2. Apply keto-enol tautomerism to amide O H O-+ H + O H keto enol NH O H NH O H amide 3. Chemiluminescence of luminol by oxidation NH NH NH 2 O O OH-N-N-NH 2 O O luminol fluorophore: blue fluorescence N N NH 2 O-O-H 2 O 2 K 3 Fe(CN) 6 O O NH 2 O-* O-+ N 2 O O NH 2 O-* O-Intersystem crossing O O NH 2 O-* O-O O NH 2 O-O-+ h v (light) triplet excited state singlet excited state ground state
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This note was uploaded on 10/16/2008 for the course CHEM 201 taught by Professor Richard during the Fall '07 term at SUNY Buffalo.