Exp Luminol - TA: HSIEN-PO CHIU Nov 13 & 15, 2007...

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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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