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BASF-14-12-2007 A) Industrial internship at Kodak Microreactor study of the Wittig reaction and Organic synthesis of porphyrin tapes Supervisor : Dr Newington.

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Presentation on theme: "BASF-14-12-2007 A) Industrial internship at Kodak Microreactor study of the Wittig reaction and Organic synthesis of porphyrin tapes Supervisor : Dr Newington."— Presentation transcript:

1 BASF A) Industrial internship at Kodak Microreactor study of the Wittig reaction and Organic synthesis of porphyrin tapes Supervisor : Dr Newington Kodak, R&D department Harrow, United Kingdom September June 2003

2 BASF Contents 1)Microreactor study of the Wittig reaction 2) Organic synthesis of porphyrin tapes

3 BASF A microreactor is a network of micron sized interconnecting channels (rectangular cross-section, depths :  m, widths :  m) Each reagent are dissolved in a specific solvent and introduced in a reservoir at the end of each channels. The mobility of solutions is allowed thanks to Electro-osmotic flow. The speed is directly proportional to the applied potentials between each reservoir and the terminal one. Reagent A Reagent B Reagent C Solvent What is a microreactor and how it works ?

4 BASF Study of Wittig reaction in microreactor All reagent are dissolved in methanol (50  L ) => Optimization of the yield

5 BASF Full factorial experimental plan T(terminal reservoir) = 0V

6 BASF Conclusion : Wittig reaction in microreactor Results of the work : The product is obtained and the yield depends on the applied potential The results was optimized due to statistical plan Advantages : Very small amount of starting material (toxic, expensive…) Very fast syntheses and easy to optimize Good spatial and temporal control of reagents. Possible to run continuously

7 BASF Organic synthesis of porphyrin tapes Target molecule : monomer, dimer and trimer of porphyrin 0, 1, 2,… R = alkyl chain Strategy : 1) Synthesis of ballast group and of dipyrromethanes 2) Formation of porphyrines monomer with metal 3) Coupling reaction

8 BASF Main properties : Intense electronic absorption and emission ( Small HOMO-LUMO energy gap) Flexible tunability of their optical and redox properties by appropriate metallation Problems : Poor solubility Difficult separations Porphyrin arrays display extremely red-shifted absorption bands in the nm region It enables to tune their optical and electronic properties in a predictable manner through the length of the arrays. The change of ballast groups in the meso-positions must be achieved in order to improve the solubility. The interest of the porphyrin Tapes

9 BASF ) Synthesis of the ballast group R = Alkyl chain

10 BASF ) Synthesis of dipyrromethanes

11 BASF ) Indirect synthesis of porphyrin monomer

12 BASF ) Direct synthesis of porphyrin monomer

13 BASF ) Coupling reactions of porphyrins 76% Poor yield

14 BASF ) Coupling reactions of porphyrins 99%

15 BASF ) Coupling reactions of porphyrins X= Br or I Ar = 3,5-dialkyloxyphenyl-

16 BASF ) Coupling reactions of porphyrins X= Br or I Ar = 3,5-dialkyloxyphenyl-

17 BASF ) Synthesis of porphyrin tapes

18 BASF Conclusion on porphyrin tapes  Targeted molecules were obtained but the yield need to be optimized  IR spectra need to be recorded This project was carried on by the next trainee but it has been given up six month later !!!


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