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5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy]phenyl]-21H,23H-porphyrin and Its Platinum and Palladium Complexes.

Byline: Yao Li and Binbin Wang

Summary: A 5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy]phenyl]-21H,23H-porphyrin (3a) and its platinum (3b) and palladium (3c) complexes are prepared and characterized by 1HNMR spectra, MS, elemental analyses, infrared spectra, Raman spectra and UV-Vis spectra. Their spectroscopic properties are further reaearched by using fluorescence spectra and high fluorescence quantum yields are found. The emission intensity of platinum 5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy]phenyl]porphyrin can be efficiently quenched by oxygen molecules in dichloromethane solution.

Keywords: Porphyrin; Synthesis; Platinum; Palladium; Fluorescence.

Introduction

Over the past decades, porphyrin and their complexes have received large attention owing to their chemical stability and specific physical and chemical properties. Numerous fields such as catalysis [1-5], optoelectronic devices [6-8], photodynamic therapy [9-12], molecular logic devices [13-16], sensors [17-19], supramolecular self-assembly [20-23] and solar energy harvesting and storages [24-26] are being conducted to use porphyrin and their complexes. The extended I-conjugation system [27-29] in porphyrin skeleton leads a wide range visible light absorptions and p-type properties as an electronic system. Porphyrins have various states in nature, which act as centers of energy / charge transfer processes.

In recent years, platinum porphyrin complexes have been studied, including as a most promising red emitting dopants for OLEDs [30, 31], as a luminescent complexes for optical oxygen sensors [32]. The platinum porphyrin complexes can be functionalized by a variety of substituent groups, which allows a fine tuning of the optical properties [33-35]. In order to further exploite optical properties, the conductive polymers with large Forster radius and high energy is used to blend with platinum porphyrin complexes to enhance the energy transfer processes to guest molecules [36, 37]. The carbazole group not only can strengthen hole transport abilities of the complexes, but also allow for an efficient transport of the absorbed energy to the core. Some carbazole functionalized metal complexes are designed, and high power efficiency was obtained [38, 39]. Several soluble metal porphyrin complexes which obtained by incorporating carbazole side groups and metal porphyrin core are reported [40].

In our study, we synthesize a 5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl]-21H,23H-phrphyrin and its platinum and palladium complexes. These compounds are characterized by using 1HNMR spectra, MS, elemental analyses, Infrared (IR), Raman, UV-Vis spectra and fluorescence behavior of these compounds are investigated. The above studies will provide a much wider prospect for choice and application of the materials.

Experimental

Materials

All reagents and solvents were of commercial reagent grade and used without purification except DMF, which was pre-dried over activated 4 A molecular sieves and vacuum distilled from calcium hydride (CaH2) prior to use. Dry benzonitrile was obtained by distillation from CaH2. Anhydrous potassium carbonate was dried under vacuum at 80AdegC for half an hour.

Apparatus and measurements

1H NMR spectra were acquired on a Varian Clnity 300MHz spectrometer by using standard pulse sequences. Spectra were recorded at 298 K in CDCl3 unless otherwise stated. Chemical shifts were reported on the I' scale relative to tetramethylsilane (TMS). Mass spectra were obtained using a VG-Quattro mass spectrometer. Thin layer chromatography was performed on glass micro-plates coated with silica gel G. Elemental analyses were measured by a Perkin-Elmer 240C auto elementary analyzer. Infrared spectra were recorded on a Nicolet 5PC-FT-IR spectrometer in the region 4000-400 cm-1.

Resonance Raman spectra were obtained with a Renishaw in via Microscopic instrument. Radiation of 514.5 nm was obtained from an Ar+ laser. UV-Vis spectra were collected on a Shimadzu UV-365 spectrometer. The photoluminescence (PL) spectrawere obtained by a Hitachi F-4500 fluorescence spectrophotometer equipped with a monochromator (resolution: 0.2 nm) and a 150W Xe lamp as the excitation source. The photoluminescence quantum yield is defined as the number of photons emitted per photon absorbed by the system and was measured with an integrating sphere by literature method [41].

Synthetic procedures

The synthesis procedures for the porphyrin derivatives were illustrated in Scheme-1.

9-(4-bromobutyl)-9H-carbazole (1)

9-(4-bromobutyl)-9H-carbazole was synthesized according to the literature procedures [42].

5, 10, 15, 20-tetrakis(4-hydroxyphenyl)porphyrin(2)

5, 10, 15, 20-tetrakis(4-hydroxyphenyl) porphyrin was synthesized according to the literature procedures [43].

5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl]-21H,23H-porphyrin (3a)

Under nitrogen, compound 2 (0.80 g, 1 mmol) was added to 250 mL of DMF with K2CO3 (1.4 g, 10 mmol). The mixture was heated to reflux for 1 h, and then compound 1 (2.4 g, 8 mmol) was added. Heating the mixture to reflux for 24 h was continued. After distilling off DMF, the residue was purified by column chromatography using silica gel with dichloromethane as eluent (yield 25%). 1H NMR (300 MHz, CDCl3, 25 AdegC, TMS): I' = 8.835 (8H, s, pyrrole ring), 8.431-8.478 (8H, t, -C6H4), 8.142-8.168(8H, d, carbazole ring C1-H), 8.069-8.096(8H, d, m-C6H4), 7.545 (8H, t, carbazole ring C2,3-H), 7.236-7.276 (16H, t, carbazole ring C4-H), 4.548-4.569 (8H, t, -O-CH2-), 4.221-4.261 (8H, t, --N-CH2-), 2.259- 2.309 (8H, m,-N-C-CH2-), 2.027-2.073 (8H, m, -O-C-CH2-), -2.785 (2H, s, pyrrole N-H). MS m/z (%): found [M+] 1563.8, calcd 1563.9.

Platinum

5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl]porphyrin (3b)

Under nitrogen, PtCl2 (50 mg, 0.2 mmol) and compound 3a (30 mg, 0.02 mmol) were suspended in 100 mL of benzonitrile. The mixture was then heated to reflux for 10 h. The mixture was cooled to room temperature, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography using silica gel with dichloromethane as the eluent (yield 99%).

Palladium

5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl]porphyrin (3c)

Complex 3c was prepared by the same procedure as complex 3b (yield 98%).

Table-1: Elemental analysis data of compounds 3a, 3b and 3c.

Compounds###Empirical###C (%)*###H (%)*###N (%)*

###formula

###3a###C108H90N8O4###82.90(82.94)###5.85(5.80)###7.13(7.16)

###3b###C108H88N8O4Pt 73.79(73.83)###5.09(5.05).###6.35(6.38)

###3c###C108H88N8O4Pd 77.78(77.75)###5.28(5.32)###6.70(6.72)

Results and Discussion

Chemistry

As a perusal of literature, the compound 1 was carried out by J. Heller et al. in 1964 and it is reported that 9-(4-bromobutyl)-9H-carbazole was synthesized with carbazole and 1, 4-dibromobutane in N, N-dimethylformamide (DMF) at 600 for 24 h [42]. On the other side, Guo et al. described the synthesis of compound 2 obtained from the reactions of 4-hydroxybenzaldehyde with pyrrole [43]. Futhermore, the nucleophilic displacement reaction of compound 1 with 2 in DMF afforded compound 3a as the products. The complexes 3b and 3c were synthesized with 3a and PtCl2 and PdCl2, respectively.

IR spectra

The partial IR frequencies and assignments of compound 3a and the corresponding complexes 3b and 3c are listed in Table-2. The two bands of 3315 and 966 cm-1 in the compound 3a are attributed to N-H stretching vibration and porphyrin core binding vibration, respectively. But these bands in the relative complexes 3b and 3c disappear since metal ions replaced the two hydrogen atoms in the N-H bonding [44]. In addition, the bands at 997 and 802 cm-1 of compound 3a is assigned to the Ip mode, which is apparent up-shifted to 1007 cm-1 and 811 cm-1 in complex 3b, up-shifted to 1008 cm-1 and 809 cm-1 in compound 3c, respectively, which exhibits the metalloporphyrin characteristic. The bands at around 1244-1248cm-1 are ascribed to Ar-O-C stretching vibration. The straight alkyl chain of porphyrin compounds include over four carbons, so the bands at around 721 cm-1 can be assigned to the methylene in-plane vibration.

Table-2: Partial infrared spectra data of compounds 3a, 3b and 3c(cm-1).

3a###3b###3c###Assignment

3315###N-H (pyrrole)

3049###3050###3049###C-H(benzene)

2924###2925###2925###C-H

2854###2854###2854###C-H

1599###1599###1599###Cm-C, C-N, C=C

1464###1459###1465###C=N

1329###1328###1330###=CN(pyrrole)

1248###1245###1244###Ar-O-C

1174###1174###1176###C-H

997###1007###1008###(p)

966###N-H (pyrrole)

802###811###809###(p)

721###725###726###C-H (CH2)n

Raman spectra

The Raman spectra are excited at 514.5 nm for porphyrin ligand and metalloporphyrin complexes. The representative peaks and their assignments are listed in Table-3. Fig. 1 exhebited the Raman spectra of the compounds 3a and 3b. In high-frequency region, the peaks of porphyrin ligand and metalloporphyrins generally arise from the totally symmetric vibrational modes. The position of peaks within the high-frequency region are very sensitive to the core size, electron density and axial ligation of the central metal ion [45-47]. A few modes are shifted in the metalloporphyrins relative to the porphyrin ligand. The band at 1551 cm-1 of compound 3a is assigned to C[beta]-C[beta] stretch 2 mode, which is apparent up-shifted to 1553 cm-1 in complexes 3b and 3c, this indicates that the symmetry of the molecule transformed from D2h to D4h.

The bands at 1492 cm-1 of compound 3a is ascribed to the phenyl ring vibration, which has little shift in complexes, indicating the metal ion almost has no influence on phenyl at meso positions. The peaks at 1361 cm-1 of compound 3a are assigned to the 4 mode. The 4 mode of complexes 3b and 3c appears at 1369 cm-1, 1368 cm-1, respectively. The 1239 cm-1 peak of compounds 3a, 3b and 3c are assigned to Cm-ph stretch 1 mode. The peak at 1079 cm-1 of compound 3a is assigned to the vibration of pyrrole C[beta]-H stretching 9 mode, which shifts to 1074 cm-1, 1073 cm-1 in complexes 3b and 3c, respectively. The peak at 1001 cm-1 of compound 3a is assigned to the vibration of pyrrole breathing and phenyl stretching 15 mode, up-shifting to 1004 cm-1 in complex 3b and down-shifting to 999 cm-1 in complex 3c.

The peak at 962 cm-1 of compound 3a is assigned to breathing 6 mode of pyrrole, however, this peak disappeared in metalloporphyrins because metal ion replaced the hydrogen atom in the N-H bonding. In low-frequency region, there is a great difference between the peaks of metalloporphyrin and porphyrin ligand, because of the structures or vibrational dynamics, especially the C[alpha]CmC[beta] bond-angles altered by metal ions. The weak Raman peak of compound 3a at 331 cm-1 was assigned to the 8 mode, which is apparent up-shifted to 379 cm-1 in complexes 3b and 3c. The 8 mode consisting the pyrrole in-plane translational motion, is described as a uniform breathing of the whole porphine ring accompanied with an in-plane deformation of C[alpha]CmC[beta] in the pyrrole ring [48].

Table-3: Raman spectra Data of compounds 3a, 3b and 3c(cm-1).

###3a###3b###3c###Mode number Assignment

1551vs###1553vs###1553vs###v2###vC[beta]-C[beta]

1492m###1492m###1492m###5###phenyl

1453m###1455m###1455m###v3###vC[alpha]C[beta]

1361w###1369vs###1368vs###v4###vC[alpha]-N/vC[alpha]C[beta]

1239m###1239m###1239m###v1###vCm-Ph

1137w###1173w###1189w###6###vCm-Ph

1079w###1074m###1073m###v9###vC[beta]-H

1001m###1004m###999m###v15###vC[alpha]C[beta]/vC[alpha]-N

###962w###v6###[beta]N-H(pyrrole)

###886w###886w###v7###phenyl

###331w###379w###379w###v8###vN-M

UV-visible absorption spectra

The UV-Vis absorption bands of porphyrins are decided by the electronic transitions which from the ground state (S0) to the two lowest singlet excited states (S1 and S2) [43]. The transition of S0 to S1 causes the weak Q bands in visible region, while the transition of S0 to S2 produces the strong Soret band in near UV region [49, 50]. The absorption spectra of compound 3a and its complexes 3b and 3c in dichloromethane (CH2Cl2) solution (1x10-5 mol/L) Fig. 2. The compound 3a showed a typical band at 421 nm for Soret band, and the Q bands appeared at 518, 554, 593, 650 nm, respectively. The transitions of Qx(0,0), Qx(0,1), Qy(0,0), Qy(0,1) result in four typical r absorptions of Q bands.

The Soret band at 421 nm is the strongest, which is much stronger than the Q bands, while the relative intensities of Q bands are in the sequence of 518>554>593>650 nm. The above Soret band and Q bands have similar intensities to that of the meso-tetrakis(phenyl)porphyrin (TPP)[51]. The porphyrin ligand absorption bands and relative intensities are very similar to that of TPP, which indicates that the covalent linking of carbazole side groups to TPP almost hasn't any effect to the porphyrin I-electron system. The absorption bands of complex 3b are almost identical too, which appear at 429, 523, 560 nm. The absorption bands of complex 3c appear at 431, 536, 569nm. Compared with the porphyrin ligand, the metalloporphyrin complexes absorption bands decrease, the obvious difference was the absence of some Q bands.

When the protons on the N atoms in pyrrole rings are substituted by the metal ions, the molecule symmetry changed from D2h to D4h, resulting some absorption spectra changes.

Fluorescence spectra

The excited-state processes of porphyrins have important significance for the application in molecular devices. The fluorescence spectra of compounds 3a, 3b and 3c in degassed dichloromethane solution (1x10-5 mol/L) were recorded at room temperature. The emission spectra of compounds 3a, 3b and 3c in degassed dichloromethane solution with the excitation wavelength of 420 nm are showed in Fig. 3. The corresponding data are listed in Table-4. The fluorescence of S2 (Soret band) and S1 (Q band) exist in porphyrin compounds. The S2 fluorescence should be attributed to the transition of S2 to S0, which is from the second excited singlet state S2 to the ground state S0, corresponding with the soret band of the UV-Vis spectra.

Additionally, S1 band can be attributed to the transition of S1 to S0, which is from the lowest excited singlet S1 to the ground state S0. The fluorescence intensity of S1 to S0 is much stronger than that of S2 to S0, owing to the resorption of strong soret band and light scattering.

Table-4: Emission spectra data and quantum yields (f) of compounds 3a, 3b and 3c.

###Compounds###max / nm###f

###3a###656###0.246

###3b###654###0.202

###3c###654###0.039

In this work, the S2 to S0 fluorescence is too weak to be observed, while the S1 to S0 fluorescence has only one band Q (0, 0), and the Q (0, 0) of compounds 3a, 3b and 3c are in the regions of 656, 654 and 654 nm, respectively. The shape of fluorescence spectra is similar with Q (0, 0) band, exhebiting a mirror symmetric to the Qx(0, 0) absorption bands. Compared with the fluorescence band of TPP at 653 nm, the emission bands of compounds 3a, 3b and 3c shows red shift by 1-3 nm, meaning a energy transfer between the carbazole ring and porphyrin ring. As showed in Fig. 4, the compound 3a exhebits a higher fluorescence intensity than that of complexes 3b and 3c. The results confirm that the fluorescence of porphyrin is quenched by the transitional metal in centre of porphyrin [52-54].

The room-temperature fluorescence quantum yields of compounds 3a, 3b and 3c in degassed CH2Cl2 solution have been confirmed by comparing with the known fluorescence yield from PtTPP (I = 0.046) [34]. Sample and standard solutions were degassed with no less than four freeze-pump-thaw cycles. The flolowing equation is used to identify the quantum yield [43].

(Equation)

Where Fi is the integral areas of fluorescence, Ai represents the absorbances and Ii represents the quantum yields at same excitation wavelength. Sample is the compounds 3b and PtTPP is the reference. The quantum yield of S1aS0 depends on the ratio between radiative process of S1aS0 and the radiationless processes of S1~aS0 and S1~aTn. The fluorescence quantum yields of 3a and 3b in solution are 0.246 and 0.202 at a concentration of 1.0x10-5 mol/L, which are much more than that of TPP [55] and PtTPP [34]. This indicates that the S1 to S0 radiative is the predominant process in these porphyrin compounds and compounds 3a and 3b possess good fluorescence properties in anaerobic surroundings. The raise of quantum yield can be explained by the insertion of carbazole group with strong hole transport.

As shown in Fig. 4, the complex 3b shows much weaker emission intensity than that recorded in oxygen free solutions under atmosphere. The experiment results suggest that in solution condition, oxygen molecules could effectively quench the fluorescence of complex 3b, indicating an oxygen-sensing property of complex 3b [56].

Conclusion

A 5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl]-21H,23H-porphyrin and its platinum and palladium complexes were synthesized and characterized. The fluorescence results presented that when platinum and palladium existed in the central of porphyrin ring, the fluorescence of porphyrin was quenched. Comparing with porphyrin ligand and its platinum complex of these type there are great fluorescence quantum yield which is attributed to the strong hole transport carbazole group. The fluorescence of platinum 5,10,15,20-Tetrakis[4-[4-(9H-carbazole-9-yl)butoxy] phenyl] porphyrin is rapidly quenched by oxygen indicating an oxygen-sensing property.

In this paper our interests are focused on the spectroscopic properties of porphyrin and its platinum and palladium complexes, investigation of the detailed fluorescence and fluorescence quantum yield of porphyrin complexes and further oxygen-sensing properties of the Pt-porphyrin/mesoporous silica system by using mesoporous materials are under way.

Acknowledgements

This work was supported by Academician workstation Innovation Foundation (13160093/010), Doctoral Foundation (660107/017) and Henan Province Colleges and Universities Key Research Project (18A620002, 18A150005).

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Author:Li, Yao; Wang , Binbin
Publication:Journal of the Chemical Society of Pakistan
Article Type:Technical report
Date:Jun 30, 2018
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