Macrocyclic Synthesis Report
Prelab 5B Macrocyclic Synthesis
OBJECTIVE:
The objective this week is to produce Tetraphenylporphyrin and its metal complex. This will be carried out by condensation of 4 equivalents of Benzaldehyde and pyyrole in the presence of propanoic acid. The product will undergo UV/Visible Spectrum tests to determine its lambda max. The lambda max will show us the relationship between a conjugated system and the visible spectrum.
PROCEDURE:
Step 1: preparation of meso-tetraphenylporphyrin (TPP)
1. Set up reflux apparatus: -Add 40 mL of propanoic acid to 100 mL RBF with boiling chips -Attach claisen head to RBF with metal clip -Attach side arm of claisen head to reflux condenser -Attach blue cap and septum to straight arm of claisen head …show more content…
Simultaneously add .7 mL (.68g, 10 mmol) of pyrrole and 1.0 mL (1.05g, 10mmol) benzaldehyde through the condenser with graduated syringes.
3. Continue to heat at reflux for 30 min.
WORK-UP
1. Cool mixture to room temp. “if low crystals, can add a little methanol and cool”
2. collect colored product by suction filtration, filter twice if needed
3. wash with methanol until it runs clear, then dry for several minutes.
4. determine percent yield (weight), record UV/Visible spectrum (CHCL3) and determine lambda max.
Step 2: Preparation of TPP Copper Complex
1. Place 10mL of N,N-dimethylformamide (DMF) in a 25mL Erlenmeyer flask with boiling chips and heat on hotplate until slight boil.
2. Add 100 mg (0.16 mmol) TPP to the hot DMF, and dissolve
3. Add ~40 mg (0.20 mmol) of Copper (II) acetate, continue to heat at reflux for 5 min.
OBJECTIVE:
The objective this week is to produce Tetraphenylporphyrin and its metal complex. This will be carried out by condensation of 4 equivalents of Benzaldehyde and pyyrole in the presence of propanoic acid. The product will undergo UV/Visible Spectrum tests to determine its lambda max. The lambda max will show us the relationship between a conjugated system and the visible spectrum.
PROCEDURE:
Step 1: preparation of meso-tetraphenylporphyrin (TPP)
1. Set up reflux apparatus: -Add 40 mL of propanoic acid to 100 mL RBF with boiling chips -Attach claisen head to RBF with metal clip -Attach side arm of claisen head to reflux condenser -Attach blue cap and septum to straight arm of claisen head …show more content…
Simultaneously add .7 mL (.68g, 10 mmol) of pyrrole and 1.0 mL (1.05g, 10mmol) benzaldehyde through the condenser with graduated syringes.
3. Continue to heat at reflux for 30 min.
WORK-UP
1. Cool mixture to room temp. “if low crystals, can add a little methanol and cool”
2. collect colored product by suction filtration, filter twice if needed
3. wash with methanol until it runs clear, then dry for several minutes.
4. determine percent yield (weight), record UV/Visible spectrum (CHCL3) and determine lambda max.
Step 2: Preparation of TPP Copper Complex
1. Place 10mL of N,N-dimethylformamide (DMF) in a 25mL Erlenmeyer flask with boiling chips and heat on hotplate until slight boil.
2. Add 100 mg (0.16 mmol) TPP to the hot DMF, and dissolve
3. Add ~40 mg (0.20 mmol) of Copper (II) acetate, continue to heat at reflux for 5 min.