Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?

Nakano, Masahiro; Shoji, Shuichi; Houchin, Y.; Osaka, Itaru; Miyazaki, Eigo; Takimiya, Kazuo

doi:10.1039/c2cc31546g

Cited by 25 publications

(20 citation statements)

References 41 publications

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“…[ 281,282 ] NDFs have four isomeric structures with linear‐shaped NDF1 and NDF2, angular‐shaped naphtho‐[1,2‐b;5,6‐b′]difuran (NDF3) and naphtho[2,1‐b;6,5‐b′]difuran (NDF4) ( Figure ). [ 283,284 ] Despite the structural similarity, their electronic structures are significantly different and depend largely on the molecular shapes.…”

Section: Naphthodifurans‐based Materials Used In Oscsmentioning

confidence: 99%

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Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Zheng

Huo

2021

Small Methods

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The state‐of‐the‐art bulk‐heterojunction (BHJ)‐type organic solar cells (OSCs) have exhibited power conversion efficiencies (PCEs) of exceeding 18%. Thereinto, thiophene and its fused‐ring derivatives play significant roles in facilitating the development of OSCs due to their excellent semiconducting natures. Furan as thiophene analogue, is a ubiquitous motif in naturally occurring organic compounds. Driven by the advantages of furan, such as less steric hindrance, good solubility, excellent stacking, strong rigidity and fluorescence, biomass derived fractions, more and more research groups focus on the furan‐based materials for using in OSCs in the past decade. To systematically understand the developments of furan‐based photovoltaic materials, the relationships between the molecular structures, optoelectronic properties, and photovoltaic performances for the furan‐based semiconductor materials including single furan, benzofuran, benzodifuran (BDF) (containing thienobenzofuran (TBF)), naphthodifurans (NDF), and polycyclic furan are summarized. Finally, the empirical regularities and perspectives of the development of this kind of new organic semiconductor materials are extracted.

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Section: Naphthodifurans‐based Materials Used In Oscsmentioning

confidence: 99%

“…Subsequently, the following methods are similar with NDF1, until the cyclization step modify to use tetrabutylammonium fluoride. [ 284 ]…”

Section: Naphthodifurans‐based Materials Used In Oscsmentioning

confidence: 99%

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Zheng

Huo

2021

Small Methods

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“…最近, Qian 等 [5] 以苯并二呋喃(BDF)为核, 引入苯上带有氟和烷氧链的基团得到了 BDF 的衍生物, 并与吡咯并吡咯二酮(DPP)反应得到了如图 3 的小分子化合物 M2, M2 的 HOMO 能级为-5.79 eV, 最低未占分子轨道 (LUMO)能级为-3.77 eV, E g 为 2.02 eV, 其噻吩类似物的 HOMO 能级为-5.80 eV, LUMO 能级为-3.83 eV, 带隙为 1.97 eV, 采用空间电荷限制电流(SCLC)法测得 M2 薄膜的空穴迁移率达到 3.7×10 -4 cm 2 •V -1 •s -1 , 电子迁移率达到 5.0×10 -4 cm 2 •V -1 •s -1 , 应用在 OSC 中 PCE 达到 5.5%, 对应的短路电流 J sc ＝11.4 mA•cm -2 , V oc ＝0.80 V, 填充因子 FF＝0.60, M2 的效率是其噻吩类似物的两倍, 这主要是因为其 J sc 是噻吩类似物(J sc ＝5.5 mA• cm -2 )的两倍导致的, M2 形貌较好, 有利于激子和电荷的分离, 同时 M2 的溶解性也要优于噻吩类似物. 随后, Nakano 等 [7] 发现, 角状的萘并二呋喃(NDF) 系列的电子结构和它们对应的萘并二噻吩(NDT)系列明显不同(如图 5), 这主要是由于不同最外层芳香环的电子对角状 NDF 和对应的 NDT 差异明显, 这种差异的本质可以归因于呋喃和噻吩的芳香性及电负性不同, 且强烈地影响到了整体稠环的电子结构. NDF1 (M5) 的 HOMO 能级为-5.5 eV, LUMO 能级为-2.1 eV, 其类似的噻吩结构的 HOMO 能级为-5.3 eV, LUMO 能级为 -2.3 eV; 角状结构 NDF3 (M6)与 M5 相比, HOMO 能级更低一点为-5.6 eV, LUMO 能级相同, 而类似的角状噻吩结构的能级都比 M6 低, 且 HOMO 能级降到了-5.8 eV, NDF3 (M7)能级与 M6 的相似, 但 M7 的噻吩相似化合物与 M6 的噻吩相似化合物的能级都要高一些.…”

Section: 呋喃稠环小分子化合物unclassified

Research Progress of the FuranContaining Fused Ring Conjugated Organic Molecules and Polymers

Liu¹,

Yuan²,

Zou³

et al. 2017

Acta Chim. Sinica

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Currently, as organic semiconductor materials, thiophene fused ring derivatives and the related polymers have received considerable research and application. Furan has similar chemical structure and electronic properties with thiophene due to the same main group heterocyclic atom in five-membered ring system. But furan and furan derivatives possess smaller aromaticity, higher carrier mobility, higher fluorescence quantum efficiency and better solubility, thus more and more attentions have been paid to the design and synthesis of furan-containing fused rings for the application in organic optoelectronic materials. This paper reviewed the recent research progresses of the synthetic methods, properties and applications of the conjugated organic small molecules and polymers based on the furan-containing fused rings. Keywords furan-containing fused rings; organic semiconducting material; five membered ring; conjugated organic small molecules; conjugated polymers

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“…[39][40][41][42] Considerable attention is currently being given to furan as a basic building block for organic p-conjugated materials that are more stable and that have given an indication of their potential applications, especially in OFETs and OLEDs. 19,[43][44][45][46][47][48] Binaphtha-furanyl has been reported as an OLET. 19 Recently, diphenyl-naphtho[2,1-b:6,5-b 0 ]difuran (DPNDF) has been experimentally synthesized and reported as a good hole transport OSM for OFETs.…”

Section: Introductionmentioning

confidence: 99%

Influence of push–pull configuration on the electro-optical and charge transport properties of novel naphtho-difuran derivatives: a DFT study

et al. 2014

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We present a density functional theory (DFT) study pertaining to electro-optical and charge transport properties of two novel derivatives of diphenyl-naphtho[2,1-b:6,5-b 0 ]difuran (DPNDF) as investigated based on push-pull configuration. Both molecular structures of the designed derivatives were optimized, in ground state (S 0 ) as well as excited state (S 1 ), using DFT and time-dependent DFT (TD-DFT) respectively. The push-pull configuration effect was studied meticulously for different electro-optical properties including adiabatic/vertical electron affinity (EAa/EAv), adiabatic/vertical ionization potential (IPa/IPv) and hole/electron reorganization energies (l h /l e ), hole/electron transfer integrals (V h /V e ), hole/ electron mobility and photostability. We observed smaller l e , improved V e and higher electron mobility for compound 1 compared with the parent molecule. Our calculated value of the electron mobility for compound 1 (2.43 cm 2 V À1 s À1 ) revealed it to be an efficient electron transport material. Moreover, the influence of the push-pull on the electronic structure was also investigated by calculating the total and partial density of states (DOS). Taking advantage of the strong push-pull configurations effect on other properties, the study of the designed chemical systems was extended to their nonlinear optical (NLO) properties. Our designed novel derivatives (1 & 2) exhibited significantly larger amplitude values for first hyperpolarizability with b tot equal to 209.420 Â 10 À30 esu for compound 1 and 333.830 Â 10 À30 esu for compound 2. It was found that the first hyperpolarizability and HOMO-LUMO energy gap are in an inverse relationship for compounds 1 and 2.

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Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?

Cited by 25 publications

References 41 publications

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Research Progress of the FuranContaining Fused Ring Conjugated Organic Molecules and Polymers

Influence of push–pull configuration on the electro-optical and charge transport properties of novel naphtho-difuran derivatives: a DFT study

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