4,4',4″,4″'-(Porphine-5,10,15,20-tetrayl)tetrakis(benzenesulfonic acid)

• CAS: 35218-75-8
• Catalog Number: ACM35218758
• Category: Main Products
• Molecular Weight: 934.44
• Molecular Formula: C44H30N4O12S4
• Synonyms: meso-Tetraphenylporphine-4,4′,4″,4″′-tetrasulfonic acid
• Appearance: Solid

Case Study

4,4',4'',4'''-(Porphine-5,10,15,20-tetrayl)tetrakis(benzenesulfonic acid) as a Sulfonated Porphyrin Ligand for Gadolinium-Based MOF Spherical Particles

Zhao, Yuewu, et al. Chemistry of Materials 30.21 (2018): 7511-7520.

4,4',4'',4'''-(Porphine-5,10,15,20-tetrayl)tetrakis(benzenesulfonic acid) (TPPS) is a water-soluble porphyrin derivative bearing sulfonate groups. When coordinated with Gd3+ ions under solvothermal conditions, it forms spherical metal-organic framework (MOF) particles rather than the two-dimensional nanosheets obtained with the analogous carboxylate ligand (TCPP), highlighting the critical role of the functional group geometry in directing MOF morphology.
Synthesis and Coordination: TPPS (5 mmol/L in DMF) was reacted with GdCl3 (5 mmol/L aqueous solution) at 60 °C for 4 h under stirring. The resulting purple-red product was collected by centrifugation, washed with ethanol and dried. The sulfonate groups exhibit higher steric hindrance and a symmetric binding range compared to carboxylates, forcing coordination in three dimensions and leading to spherical aggregates.
Performance Evaluation: The Gd-TPPS MOF particles showed a longitudinal relaxivity of 16.73 /mM/s at 0.5 T, which is lower than that of the Gd-TCPP nanosheets (40.8 /mM/s) but still significantly higher than that of the clinical agent Gd-DTPA (4.59 /mM/s). The reduced relaxivity relative to the nanosheet analogue is attributed to the smaller particle size, lower molecular weight and different microstructure. UV-vis spectroscopy confirmed coordination through the sulfonate groups without affecting the porphyrin core.

4,4',4'',4'''-(Porphine-5,10,15,20-tetrayl)tetrakis(benzenesulfonic acid) as a Proton‑Reservoir Molecule for Ultra‑Low‑Power Organic Protonic Synapses

Liu, Shuzhi, et al. Advanced Science 10.34 (2023): 2305075.

4,4',4'',4'''-(Porphine-5,10,15,20-tetrayl)tetrakis(benzenesulfonic acid) (TPPS) is a porphyrin derivative bearing both proton-donating sulfonic acid and proton-accepting amino groups. It enables sequential proton migration and self-coordinated doping under low electric fields, allowing nonvolatile, multi-state conductance modulation with near-zero power consumption for neuromorphic computing. TPPS provides a versatile molecular platform for artificial synapses that simultaneously achieve ultra-low power and nonvolatile memory, overcoming a key challenge in neuromorphic hardware.
Device Fabrication: TPPS was synthesised by sulfonation of tetraphenylporphyrin in concentrated H2SO4 at 90 °C for 6 h. Au/TPPS/Au cross-point memristors were fabricated on SiO2/Si substrates by electron-beam lithography, with electrode linewidths from 10 μm down to 100 nm. A 5 mg/mL TPPS aqueous solution was spin-coated (4000 rpm, 60 s) and dried at 80 °C to form an 18 nm thick active layer.
Performance Evaluation: TPPS devices achieved 64 linearly distinguishable conductance states (650 fA to 82.5 pA) with retention exceeding 30 min. Modulation power ranged from 16.25 pW to 2.06 nW, while read power was as low as 6.5 fW to 0.83 pW, approaching the estimated power of biological synapses (tens of fW). The device successfully emulated spike-rate-dependent plasticity (SRDP) and spike-timing-dependent plasticity (STDP) with 0.66- 0.82 pW operation, and showed robust long-term depression/potentiation over 100 cycles with <0.3% weight variation.

Synthetic Use

Upstream Synthesis Route 1

• 88289-00-3

• 35218-75-8

Reference: [1]Shchukina, M. V.; Gnedin, B. G.; Berezin, B. D.
[Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 12.1, p. 1987 - 1994][Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 12, p. 2464 - 2472]

Upstream Synthesis Route 2

• 917-23-7

• 35218-75-8

Reference: [1]Beyene, Belete B.; Yibeltal, Amogne W.; Hung
[Inorganica Chimica Acta, 2020, vol. 513]