Synthesis and characterization of meso-tetraphenylporphyrin derivatives and their copper(II) complexes

Name: Tossapon Phromsatit

keyword: Porphyrin long chain

; ?-Nitro substituted porphyrin

; Gases sensor

Abstract: Porphyrins play a vital role in biological systems. Porphyrins and theirmetal complexes are used in many applications including catalyst, dye-sensitized solarcell, photo dynamic therapy, due to their outstanding properties such as high chemicaland thermal stability, strong absorption in visible region, and flexible architecturalmodification. Moreover, the ?-functionalization of meso-tetraphenylporphyrin is ofgreat interest since the electronic properties of the porphyrin macrocycle can be alteredby small charge in the substituents. The ?-nitration of the porphyrin ring is of specialinterest since the nitro group are versatile and can converted into several otherfunctional group.This study focus on the process of synthesis and properties of meso-aryllong chain porphyrin and their metal complexes. The meso-aryl long chain porphyrinand their derivative were synthesized by Alder-Longo method between the long chainalkyl substituents aldehyde and pyrrole. The long chain alkyl aldehyde substituentsderivatives were synthesized by refluxing 4-hydroxybenzaldehyde with bromoalkaneand K2CO3 in propionic acid. Then, the meso-aryl long chain porphyrin, includingTetraphenylporphyrin (TPP), Tetrakis(4-methoxyphenyl) porphyrin (TOMPP),Tetrakis(4-butyloxyphenyl)porphyrin (TOBPP), Tetrakis(4-octyloxyphenyl)porphyrin(2)(TOOPP), and Tetrakis(4-decyloxyphenyl)porphyrin (TODPP) were prepared. Thecopper (II) porphyrin complexes have been synthesized by refluxing the meso-alkyllong chain porphyrin with copper acetate in DMF. The results provide the followingproducts: CuTPP, CuTOMPP, CuTOBPP, CuTOOPP, and CuTODPP, respectively.Finally, The ?-nitro substituted porphyrin were prepared via nitration reaction ofcopper porphyrin complexes with Cu(NO3)2 and acetic anhydride in chloroform. TheCuTPP-NO2, CuTOMPP-NO2, CuTOBPP-NO2, CuTOOPP-NO2, and CuTODPP-NO2were obtained, respectively. The structure of all synthesized compounds wereconfirmed by 1H NMR 13C NMR UV-Vis, fluorescence, FT-IR spectroscopy, CHNelemental analysis, and mass spectrometry. The characterization shows that nitro groupis attached on to a ?-pyrrolic position of porphyrin. The thermal stability of allcomplexes were studied by thermal gravimetric analysis. The all complexes were alsotested for antibacterial activity using disc diffusion technique. The all synthesizedcompounds were found to be effective for the inhibition of bacterial growth.Furthermore, the CuTPP-NO2 was fabricated as film for the detection of alcoholvapours. The sensing properties was investigated by using \"electronic nose (e-nose)\".The Principle Component Analysis (PCA) usually chosen for presenting the patternsobserved from e-nose. Thus the result confirm that the CuTPP-NO2 has the capabilityof performing as an alcohol sensor

Thammasat University. Thammasat University Library

Address: BANGKOK

Email: preserv@tu.ac.th

Name: Supakorn Boonyuen

Role: advisor

Name: Nanthawat Wannarit

Role: co-advisor

Created: 2015

Modified: 2021-10-01

Issued: 2021-10-01

วิทยานิพนธ์/Thesis

application/pdf

DOI: 10.14457/TU.the.2015.494

eng

DegreeName: Master of Science

Level: Master's Degree

Descipline: Chemistry

Grantor: Thammasat University

©copyrights Thammasat University

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