Thienothiophene and biphenyl based conjugated porous polymer as a photocatalyst for visible light induced free radical and cationic polymerization

Isci, Recep; Gencosman, Emirhan; Yagci, Yusuf; Ozturk, Turan

doi:10.1016/j.jphotochem.2023.115427

“…The results showed that the characteristic absorption of the catalysts remained observable without any significant decrease (photodegradation), suggesting that the catalysts are renewable after the electron transfer (Figure S50). [69] 1) and ( 2) are 1 H NMR spectra of DMA in the presence of photoinitiator or NI-1, after 365 nm LED (10 mW cm À 2 ) irradiation for 60 s. ( 3) and ( 4) are 1 H NMR spectra of DMA in the presence of NI-1 and photoinitiator, after 365 nm LED (10 mW cm À 2 ) irradiation for 0 s and 60 s, respectively, in Ar, in CDCl 3 .…”

Section: Methodsmentioning

confidence: 99%

Novel Photocatalyst Based on Through‐Space Charge Transfer Induced Intersystem Crossing Enables Rapid and Efficient Polymerization Under Low‐Power Excitation Light

Liang,

Zhang,

Lu

et al. 2024

Angew Chem Int Ed

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Currently, most photoredox catalysis polymerization systems are limited by high excitation power, long polymerization time, or the requirement of electron donors due to the precise design of efficient photocatalysts still poses a great challenge. Herein, we propose a new approach: the creation of efficient photocatalysts having high ground state oxidation potentials and high excited state energy levels, along with through‐space charge transfer induced intersystem crossing (ISC) properties. Using this strategy, a cabazole‐naphthalimide (NI) dyad (NI‐1) characterized by long triplet excited state lifetime (tT = 62 μs), satisfactory ISC efficiency (ΦΔ = 54.3%) and powerful reduction capacity [Singlet: E1/2 (PC+1/*PC) = ‐1.93 eV, Triplet: E1/2 (PC+1/*PC) = ‐0.84 eV] was obtained. An efficient and rapid polymerization (83% conversion of 1 mM monomer in 30 s) was observed under the conditions of without electron donor, low excitation power (10 mW cm‐2) and low catalyst (NI‐1) loading (< 50 mM). In contrast, the conversion rate was lower at 29% when the reference catalyst (NI‐4) was used for photopolymerization under the same conditions, demonstrating the advantage of the TSCT photocatalyst. Finally, the TSCT material was used as a photocatalyst in practical lithography for the first time, achieving pattern resolutions of up to 10 μm.

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“…The results showed that the characteristic absorption of the catalysts remained observable without any significant decrease (photodegradation), suggesting that the catalysts are renewable after the electron transfer (Figure S50). [69] 1) and ( 2) are 1 H NMR spectra of DMA in the presence of photoinitiator or NI-1, after 365 nm LED (10 mW cm À 2 ) irradiation for 60 s. ( 3) and ( 4) are 1 H NMR spectra of DMA in the presence of NI-1 and photoinitiator, after 365 nm LED (10 mW cm À 2 ) irradiation for 0 s and 60 s, respectively, in Ar, in CDCl 3 . To investigate whether the polymerization systems described above have advantages over those constructed with commercial photoinitiators, we first attempted to polymerize DMA with NI-1 and DPI or 2,4,6-trimethylbenzoyldiphenyl phosphine oxide (TPO).…”

Section: Forschungsartikelmentioning

confidence: 99%

Novel Photocatalyst Based on Through‐Space Charge Transfer Induced Intersystem Crossing Enables Rapid and Efficient Polymerization Under Low‐Power Excitation Light

Liang,

Zhang,

Lu

et al. 2024

Angewandte Chemie

0

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Currently, most photoredox catalysis polymerization systems are limited by high excitation power, long polymerization time, or the requirement of electron donors due to the precise design of efficient photocatalysts still poses a great challenge. Herein, we propose a new approach: the creation of efficient photocatalysts having high ground state oxidation potentials and high excited state energy levels, along with through‐space charge transfer induced intersystem crossing (ISC) properties. Using this strategy, a cabazole‐naphthalimide (NI) dyad (NI‐1) characterized by long triplet excited state lifetime (tT = 62 μs), satisfactory ISC efficiency (ΦΔ = 54.3%) and powerful reduction capacity [Singlet: E1/2 (PC+1/*PC) = ‐1.93 eV, Triplet: E1/2 (PC+1/*PC) = ‐0.84 eV] was obtained. An efficient and rapid polymerization (83% conversion of 1 mM monomer in 30 s) was observed under the conditions of without electron donor, low excitation power (10 mW cm‐2) and low catalyst (NI‐1) loading (< 50 mM). In contrast, the conversion rate was lower at 29% when the reference catalyst (NI‐4) was used for photopolymerization under the same conditions, demonstrating the advantage of the TSCT photocatalyst. Finally, the TSCT material was used as a photocatalyst in practical lithography for the first time, achieving pattern resolutions of up to 10 μm.

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“…Thieno[3,2- b ]thiophene (TT) has a rigid structure with extended π-conjugation, which makes it suitable π-linker for adjusting the band gap of organic materials and to increase the intermolecular interactions in solid state. − It is an electron-rich molecule, making it a promising material for the construction of conjugatedlow band gap polymeric semiconductors for energy-based applications such as organic solar cells, organic light-emitting diodes, and organic field-effect transistors. − In this report, we describe supercapacitor and energy storage performances of TT-TPA-SWCNT by cyclic voltammetry (CV), galvanostatic charge/discharge (GCD), and electrochemical impedance spectroscopy (EIS). For the first time, a high-performance free-standing and flexible electrode, based on a thienothiophene (TT) derivative and SWCNT, prepared without using any nonconductive binding agent, is reported.…”

Section: Introductionmentioning

confidence: 99%

High-Performance Thienothiophene and Single Wall Carbon Nanotube-Based Supercapacitor as a Free-Standing and Flexible Hybrid Energy Storage Material

Isci,

Donmez,

Karatepe

et al. 2024

ACS Appl. Energy Mater.

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Long cycle life and high energy/power density are imperative for energy storage systems. Similarly, flexible and freestanding electrodes are important for supercapacitor applications. Herein, we report, for the first time, use of thienothiophene (TT) and a single-walled carbon nanotube (SWCNT)-based free-standing and flexible hybrid material (TT-TPA-SWCNT) as a high-performance supercapacitor. The synthesized TT derivative, TT-TPA, was directly attached to SWCNT through noncovalent interactions to obtain the TT-based SWCNT hybrid, TT-TPA-SWCNT, as a flexible film. The hybrid film was clarified by surface analysis methods of scanning electron microscopy and atomic force microscopy. TT-TPA-SWCNT was used as a flexible and free-standing electrode in a two-electrode system for supercapacitor and energy storage applications. It displayed a high energy storage capacity of 83.2 F g −1 at 5 mV s −1 scan rate, an excellent cyclic stability with 110% retention of its initial specific capacitance after 7000 cycles and a long power density ranged from 100 to 3000 W•kg −1 , demonstrating that TT-TPA-SWCNT is a promising hybrid nanomaterial for high-performance energy storage applications.

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Thienothiophene and biphenyl based conjugated porous polymer as a photocatalyst for visible light induced free radical and cationic polymerization

Cited by 10 publications

References 45 publications

Novel Photocatalyst Based on Through‐Space Charge Transfer Induced Intersystem Crossing Enables Rapid and Efficient Polymerization Under Low‐Power Excitation Light

Novel Photocatalyst Based on Through‐Space Charge Transfer Induced Intersystem Crossing Enables Rapid and Efficient Polymerization Under Low‐Power Excitation Light

Novel Photocatalyst Based on Through‐Space Charge Transfer Induced Intersystem Crossing Enables Rapid and Efficient Polymerization Under Low‐Power Excitation Light

High-Performance Thienothiophene and Single Wall Carbon Nanotube-Based Supercapacitor as a Free-Standing and Flexible Hybrid Energy Storage Material

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