Novel pyrene-based donor–acceptor organic dyes for solar cell application

Yu, Chun-Chun; Jiang, Ke‐Jian; Huang, Jinhua; Zhang, Fang; Bao, Xia; Wang, Fengwu; Yang, Lian‐Ming; Song, Yanlin

doi:10.1016/j.orgel.2012.12.013

Cited by 39 publications

(14 citation statements)

References 27 publications

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“…These DA pyrenes developed up to date can be classified into three substitution patterns: (i) at the active site of 1-, 3-, 6-, and 8positions 24−26,30,32−34 (Figure 1A), (ii) at the plane node of 2-, 7-positions 29,31,34 and the K-region of 4-, 5-, 9-, 10positions 27,28 (Figure 1B, left), and (iii) at the fusion site of 2,7-/4,5-and/or 1,8-/4,5-positions 28 (Figure 1B, right). The photophysical properties for the DA pyrenes are strikingly influenced by the ICT processes through the change of the substitution positions (see Figure 1), thereby making these molecules potential candidates as optoelectronic materials, 24,26,29 solvent polarity sensors, 28 photostable fluorophores, 32 etc. As previously mentioned, since the dynamic ICT processes essentially depend on the corresponding static π-conjugation patterns, 11−13 assuming that the change of π-conjugation directions in the dipolar organic π-conjugated molecules could be realized by the variety of the substitution patterns, in which case variable photophysical properties are achievable through the corresponding ICT process.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of Donor–Acceptor-Type 1,3,5,9-Tetraarylpyrenes: Controlling Intramolecular Charge-Transfer Pathways by the Change of π-Conjugation Directions for Emission Color Modulations

et al. 2018

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In dipolar organic π-conjugated molecules, variable photophysical properties can be realized through efficient excited-state intramolecular charge transfer (ICT), which essentially depends on the π-conjugation patterns. Herein, we report a controllable regioselective strategy for synthesis and optical properties of two donor–acceptor (DA)-type 1,3,5,9-tetraarylpyrenes (i.e., 1,3-A/5,9-D ( 4b ) and 1,3-D/5,9-A ( 4c )) by covalently integrating two phenyl rings and two p -OMe/CHO-substituted phenyl units into the 2- tert -butylpyrene building block, in which the two phenyl rings substituted at the 1,3-positions act as acceptors for 4b or as donors for 4c and the two p -OMe or p -CHO-substituted phenyl moieties substituted at the K-region of 5,9-positions act as donors for 4b or as acceptors for 4c , respectively. Density functional theory calculations on their frontier molecular orbitals and UV–vis absorption of S 0 → S 1 transition theoretically predicted that the change of π-conjugation directions in the two DA pyrenes could be realized through a variety of substitution patterns, implying that the dissimilar ground-state and excited-state electronic structures exist in each molecule. Their single-crystal X-ray analysis reveal their highly twisted conformations that are beneficial for inhibiting the π-aggregations, which are strikingly different from the normal 1,3,5,9-tetraphenylpyrenes ( 4a ) and related 1,3,6,8-tetraarylpyrenes. Indeed, experimental investigations on their optical properties demonstrated that the excited-state ICT pathways can be successfully controlled by the change of π-conjugation directions through the variety of substitution positions, resulting in the modulations of emission color from deep-blue to green in solution. Moreover, for the present DA pyrenes, highly fluorescent emissions with moderate-to-high quantum yields both in the thin film and in the doped poly(methyl methacrylate) film were obtained, suggesting them as promising emitting materials for the fabrication of organic light-emitting diodes.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of Donor–Acceptor-Type 1,3,5,9-Tetraarylpyrenes: Controlling Intramolecular Charge-Transfer Pathways by the Change of π-Conjugation Directions for Emission Color Modulations

et al. 2018

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“…In recenty ears, there has been great interesti nb otht he design and synthesis of new pyrene derivatives, especially in the context of organic electronics. Pyrene derivatives can be appliedi ne lectronic devices such as organic light-emitting diodes (OLEDs) [1][2][3][4][5][6] and organic field-effect transistors (OFETs), [7][8][9] as well as in organic photovoltaic cells (OPVs) [10] and liquid crystalline materials. [11] This broad range of applications comes from the highly p-conjugated system of the pyrene core, which provides desirable photophysical and optical properties.…”

Section: Introductionmentioning

confidence: 99%

NCN‐Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics

Zych

Kurpanik

Słodek

et al. 2017

Chemistry A European J

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Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4-(2,2-dimethylpropyloxy)pyridine (P1), 4-decyloxypyridine (P2), 4-pentylpyridine (P3), 1-decyl-1,2,3-triazole (P4), and 1-benzyl-1,2,3-triazole (P5), are obtained through a Suzuki-Miyaura cross-coupling reaction or Cu -catalyzed 1,3-dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1-P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid-state photo- and electroluminescence characteristics of selected compounds as organic light-emitting diodes are tested. In the guest-host configuration, two matrixes, that is, poly(N-vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD-DFT) provide a deeper understanding of the experimental results.

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“…Pyrene and pyrenyl derivatives among many ICT molecules have found applications in organic electronic devices such as organic thin-film transistors and organic solar cells owing to the selective functionalization ability of pyrene core. , In particular, electron donor (D) and/or acceptor (A) groups are often introduced on the pyrene core to adjust photophysical properties for a specific application. − In our previous study, we developed a series of donor–pyrene (acceptor)–donor ( DPD ) systems with different numbers of donating substituents ( N , N -dimethylaniline (DMA)) at different positions of pyrene core and elucidated the ICT dynamics . Despite the highly symmetric structure, DPD triad molecules exhibit a clear dual emission from locally excited (LE) and CT states indicating the precursor–successor type CT in the Marcus normal region.…”

mentioning

confidence: 99%

Strong Electronic Coupling-Induced Ultrafast Charge Transfer in Donor–Pyrene–Acceptor Systems

Park

Sung

Kim

2021

J. Phys. Chem. Lett.

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In this study, we decipher the charge transfer (CT) processes in donor–pyrene–acceptor (DPA) molecules via various time-resolved spectroscopic measurements. It has been challenging to unravel the ultrafast CT dynamics in DPA molecules because they exhibit an initial CT emission in the same spectral range as the locally excited (LE) emission. However, we finally observed the CT rate of ∼200 fs in DPA molecules from the time-resolved fluorescence anisotropy decay profiles. Our measurements allow us to suggest that the LE and CT states of DPA systems have isoenergetic potential surfaces and that the introduction of the acceptor to the pyrene moiety gives rise to strong electronic coupling between the LE and CT states. Therefore, we determined that this solvent-independent ultrafast CT occurs through the adiabatic potential energy surface and that the CT characteristics are enhanced in DPA compared to the donor–pyrene–donor system.

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Novel pyrene-based donor–acceptor organic dyes for solar cell application

Cited by 39 publications

References 27 publications

Synthesis and Optical Properties of Donor–Acceptor-Type 1,3,5,9-Tetraarylpyrenes: Controlling Intramolecular Charge-Transfer Pathways by the Change of π-Conjugation Directions for Emission Color Modulations

Synthesis and Optical Properties of Donor–Acceptor-Type 1,3,5,9-Tetraarylpyrenes: Controlling Intramolecular Charge-Transfer Pathways by the Change of π-Conjugation Directions for Emission Color Modulations

NCN‐Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics

Strong Electronic Coupling-Induced Ultrafast Charge Transfer in Donor–Pyrene–Acceptor Systems

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