427875-87-4

Usage

Uses

Used in Organic Electronics:
N-hexyldithieno[3,2-b:2’,3’-d]pyrrole is used as a semiconducting material for its potential applications in organic photovoltaics, field-effect transistors, and light-emitting diodes. Its unique molecular structure and ability to conduct electricity contribute to its suitability in these applications.
Used in Optoelectronic Devices:
In the optoelectronics industry, N-hexyldithieno[3,2-b:2’,3’-d]pyrrole is utilized for its potential in creating devices that can generate, detect, or control light. Its properties, such as high charge carrier mobility and good solubility, make it a valuable component in the development of advanced optoelectronic technologies.
Used in Organic Photovoltaics:
N-hexyldithieno[3,2-b:2’,3’-d]pyrrole is employed as a key component in the development of organic photovoltaics, where it contributes to the efficiency and performance of solar cells. Its ability to conduct electricity and interact with light makes it a promising material for improving the energy conversion capabilities of these devices.
Used in Field-Effect Transistors:
In the semiconductor industry, N-hexyldithieno[3,2-b:2’,3’-d]pyrrole is used as a material for field-effect transistors. Its high charge carrier mobility and good solubility properties make it suitable for creating transistors with improved performance and reliability.
Used in Light-Emitting Diodes:
N-hexyldithieno[3,2-b:2’,3’-d]pyrrole is also used in the development of light-emitting diodes (LEDs) due to its optoelectronic properties. Its ability to emit light when an electric current is applied makes it a valuable material for creating energy-efficient and long-lasting LEDs.

Upstream product

• 51751-44-1 3,3'dibromo-2,2'-bithiophene 
• 111-26-2 hexan-1-amine 
• 492-97-7 2,2'-Bithiophene 
• 125143-53-5 3,3',5,5'-tetrabromo-2,2'-bithiophene 
• 394203-42-0 N-hexyl-N-(3'-thienyl)-3-amino-thiophene 

Downstream Products

• 1261288-51-0 C₄₈H₅₅N₃O₄S₂ 

Relevant academic research and scientific papers

Starburst Triarylamine Donor-Based Metal-Free Photosensitizers for Photocatalytic Hydrogen Production from Water

Three metal-free molecular photosensitizers (S1-S3) featuring a starburst triarylamine donor moiety have been synthesized. They show attractive photocatalytic performance in visible light-driven H2 production from water in their platinized TiO2 composites. A remarkable H2 turnover number (TON) of 10 200 (48 h) was achieved in an S1-anchored system.

Functionalization of boron-doped diamond with a push-pull chromophore via Sonogashira and CuAAC chemistry

Improving the performance of p-type photoelectrodes represents a key challenge toward significant advancement in the field of tandem dye-sensitized solar cells. Herein, we demonstrate the application of boron-doped nanocrystalline diamond (B:NCD) thin films, covalently functionalized with a dithienopyrrole-benzothiadiazole push-pull chromophore, as alternative photocathodes. First, a primary functional handle is introduced on H-terminated diamond via electrochemical diazonium grafting. Afterwards, Sonogashira cross-coupling and Cu(i) catalyzed azide-alkyne cycloaddition (CuAAC) reactions are employed to attach the chromophore, enabling the comparison of the degree of surface functionalization and the importance of the employed linker at the diamond-dye interface. X-ray photoelectron spectroscopy shows that surface functionalization via CuAAC results in a slightly higher chromophore coverage compared to the Sonogashira cross-coupling. However, photocurrents and photovoltages, obtained by photoelectrochemical and Kelvin probe measurements, are approximately three times larger on photocathodes functionalized via Sonogashira cross-coupling. Surface functionalization via Sonogashira cross-coupling is thus considered the preferential method for the development of diamond-based hybrid photovoltaics.

Dialkylthienosilole and N-alkyldithienopyrrole-based copolymers: Synthesis, characterization, and photophysical study

We synthesized and characterized a set of D-π-A conjugated copolymers containing thiophene π-bridge. While benzothiadiazole serves as an acceptor (A) unit, the 4,4-dialkyldithieno[3,2-b:2′,3′-d]silole (DTSi) or N-alkyldithieno[3,2-b:2′,3′-d]pyrrole (DTP) act as a donor (D) unit. The copolymers were synthesized via the commonly Stille cross-coupling reaction and exhibited molecular weights of 18.6 to 31.3 kg/mol. The main structural differences among the copolymers are the type of donor moiety (DTSi or DTP) and the position of hexyl side chains on the thiophene π-bridge units between the D and A moieties. The ultimate goal of this work is to explore the effect of three structural factors that could control the photophysical properties of polymers in order to help in the rational design of polymers having specific properties used in optoelectronic devices. The physical properties include thermal stability, photophysical, and electrochemical properties. The structural factors are (a) the power of donor moiety, (b) the position of alkyl side chain on the thiophene π-bridge, and (c) the nature of the alkyl side chain. Also, we utilized the density functional theory calculations to calculate the geometric and electronic structures. A good agreement was remarked between the experimental and theoretical findings.

Synthesis and properties of dicyanomethylene-endcapped thienopyrrole-based quinoidal S,N-heteroacenes

A new series of highly π-extended dicyanomethyleneendcapped quinoidal S,N-heteroacenes (JH-quinoids) fused with thiophene and pyrrole rings have been designed and synthesized. The α-extension of the central S,N-heteroacene cores gives rise to significant red-shifted absorption maxima in solution without being affected by the long alkyl groups. The absorption maximum of JH10 with the longest quinoidal backbone in the thin film significantly red-shifted to the nearinfrared region of 1260nm as compared to that in solution (880 nm), indicating the formation of strong intermolecular interaction in the solid state. JH-quinoids maintain sufficiently low LUMO energy levels in the range of 14.09～4.22 eV regardless of the fused ring systems and substituents, while the HOMO energy levels increase with extending the length of S,N-heteroacenes; the highest HOMO energy level of JH10 is as high as -15.18 eV owing to the contributions from the nitrogen atoms and chalcogen. The molecular geometries of JH-quinoids optimized from the DFT calculations indicate their complete planar backbones and the trend of HOMO and LUMO energy levels variation is in good agreement with the cyclic voltammetry results. Consequently, the present JHquinoids should be promising candidates for ambipolar organic semiconductors.

Dithienopyrrole as a rigid alternative to the bithiophene π relay in chromophores with second-order nonlinear optical properties

4H-Pyranylidene-containing push-pull chromophores built around a bithiophene (BT) π relay or a rigidified thiophene-based unit, namely cyclopenta[1,2-b:3,4-b′]dithiophene (CPDT) or dithieno[3,2-b:2′,3′-d]pyrrole (DTP), have been synthesized and characterized. The effect of these different relays on the polarization and the second-order nonlinear optical (NLO) properties has been studied. For the sake of comparison, the corresponding reported dithieno[3,2-b:2′,3′-d]thiophene (DTT) derivatives have also been included in the discussion. Replacement of the BT core by a rigidified unit (CPDT, DTP) leads to more polarized systems. Calculated NBO charges and electrochemical measurements show that dithienopyrrole has a remarkable donor character that allows an important charge transfer between the donor and the acceptor. The influence of the rigidification of the BT relay on the NLO responses depends on the acceptor strength. For the weakest acceptor used (thiobarbituric acid), passing from the BT relay to the rigidified units always involves an increase in the μβ0 figure of merit. Nevertheless, for the strongest acceptor (2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF)), a slight increase in μβ0 with respect to the BT chromophore is only observed for the DTP derivative. Thus, rigidification of the BT core is not enough to improve the second-order nonlinearity and the incorporation of a DTP moiety has proven to be the most efficient approach for this purpose.

Heteroheptacenes with fused thiophene and pyrrole rings

The preparation of conjugated heteroheptacenes using an electrophilic coupling reaction induced by a super acid is reported. The new molecules containing thiophene and/or pyrrole rings are bisbenzo[b,b']thienodithieno[3,2- b:2',3'-d]pyrrole, bisbenzo[b,b']thienocyclopenta[2, l -b :3,4-b']dithiophene, and bisthieno[3,2no]thieno[2,3-f:5,4-f]carbazole. Dithieno[3,2-b:2',3'-d] pyrrole, cyclopenta[2, lb:3,4-b']dithiophene, and carbazole are used as the aromatic cores. This versatility provides access to molecules with systematically controllable physicochemical properties. Single-crystal X-ray analyses demonstrate that the type and position of the alkyl substituents significantly changes the packing properties of the new molecules. The optical and optoelectronic properties of the heteroheptacenes vary considerably depending on the number and position of the sulfur or nitrogen linkages and reveal the improved environmental stability over their hydrocarbon counterparts. The analysis of the experimental results from UV/Vis absorption/ photoluminescence (PL) spectroscopy and cyclic voltammetry were combined with DFT quantum-chemical calculations and compared with other model heteroheptacenes. The results suggest that among the acenes with the same number of fused rings, the thiophene ring fusion inside the skeleton stabilizes both HOMO and LUMO levels more effectively than pyrrole and benzene rings. The present study also shows that the new heteroheptacenes are promising candidates for the construction of electronic materials.

A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles: Fused-ring building blocks for new conjugated polymeric systems

A general synthetic route has been developed for the simple and efficient preparation of N-functionalized dithieno[3,2-b: 2′,3′-d]pyrroles. These synthetic methods utilize N-functionalized N-(3′-thienyl)-3-aminothiophenes produced from the Pd-catalyzed am