4,4′‐Spirobi[cyclopenta[2,1‐<i>b</i>;3,4‐<i>b</i>′]dithiophene: A New Generation of Heterocyclic Spiro‐Type Molecules

Londenberg, Joscha; Saragi, Tobat P. I.; Suske, Irina; Salbeck, Josef

doi:10.1002/adma.200700401

Cited by 30 publications

(29 citation statements)

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“…Indeed, 1 a the constituting building block of 1 c – g presents a first oxidation wave ${E{{1\hfill \atop {\rm ox}\hfill}}}$ at 1.47 V that is assigned to an indenofluorenyl electron transfer 26. On the other hand, literature reports for several molecules bearing the “aryl‐fluorene‐aryl” moieties such as 2,7‐bis‐(4‐ tert ‐butylphenyl)‐9,9′‐spirobifluorene38 and 2,2′,7,7′‐tetraphenyl‐9,9′‐spirobifluorene,39 a first oxidation potential ${E{{1\hfill \atop {\rm ox}\hfill}}}$ around 1.39 V vs SCE. It is hence difficult to assign the first electron transfer of 1 c – f since i) the indenofluorenyl core and the “aryl‐fluorene‐aryl” core are oxidized at similar potentials (1.47 vs 1.39 V, respectively) and ii) 1 c – f present a first oxidation potential ${E{{1\hfill \atop {\rm ox}\hfill}}}$ ranging from 1.28 to 1.45 V, depending on the substituents borne by the phenyl rings.…”

Section: Resultsmentioning

confidence: 99%

Violet‐to‐Blue Tunable Emission of Aryl‐Substituted Dispirofluorene–Indenofluorene Isomers by Conformationally‐Controllable Intramolecular Excimer Formation

Thirion

Poriel

Métivier

et al. 2011

Chemistry A European J

114

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Two series of DiSpiroFluorene-IndenoFluorene (DSF-IF) positional isomers, namely dispiro[2,7-diarylfluorene-9',6,9'',12-indeno[1,2-b]fluorenes], (1,2-b)-DSF-IFs 1 and dispiro[2,7-diarylfluorene-9',6,9'',12-indeno[2,1-a]fluorenes], (2,1-a)-DSF-IFs 2 have been synthesized. These violet-to-blue fluorescent emitters possess a 3π-2spiro architecture, which combines via two spiro links two different indenofluorene cores, that is, (1,2-b)-IF or (2,1-a)-IF and 2,7-substituted-diaryl-fluorene units. Due to their different geometric profiles, the two families of positional isomers present drastically different properties. The marked difference observed between the properties of (1,2-b)-DSF-IF (1) and (2,1-a)-DSF-IF (2) is discussed in terms of intramolecular π-π interactions occurring in (2,1-a)-DSF-IF (2) leading to conformationally-controllable intramolecular excimer formation. Indeed, the original geometry of the (2,1-a)-DSF-IF (2) family, with face-to-face "aryl-fluorene-aryl" moieties, leads to remarkable excimer emission through intramolecular π-π interactions in the excited state. Furthermore, the emission wavelengths can be gradually modulated by the control of the steric hindrance between the adjacent substituted phenyl rings. Thus, through a comparative and detailed study of the (1)H NMR, electrochemical and photophysical properties of DSF-IFs 1 and 2, we have evidenced the intramolecular π-π interactions occurring between the two "aryl-fluorene-aryl" moieties in the ground state and in the excited state. These properties have been finally correlated to the spectacular conformational change modeled by density functional theory (DFT) calculations. Indeed, the two "aryl-fluorene-aryl" moieties switch from a staggered conformation in the ground state to an eclipsed conformation in the first excited state.

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Section: Resultsmentioning

confidence: 99%

Violet‐to‐Blue Tunable Emission of Aryl‐Substituted Dispirofluorene–Indenofluorene Isomers by Conformationally‐Controllable Intramolecular Excimer Formation

Thirion

Poriel

Métivier

et al. 2011

Chemistry A European J

114

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“…[16][17][18] To date, non-fullerene acceptor-based OSCs have been reported with higher PCEs than PC 61 BM/PC 71 BM-based devices. Materials based on SCPDT have been widely used in field-effect transistors, [30] dyesensitized solar cells, [31] andp erovskite solar cells. [5] Thus, developing new types of high-performance SM acceptors is highly desired.…”

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confidence: 99%

“…[5] Thus, developing new types of high-performance SM acceptors is highly desired. [30] Due to the well-conjugated structure and electron-rich property of two cyclopenta[2,1-b;3,4-b']dithiophene(CPDTs), [34] SCPDTbased molecules are expected to show strong intramolecular charge-transfer characteristics and thus broad low-energyo ptical transitionsa nd good charge mobility.U sing the simple solution spin-coating fabrication process, ah igh PCE of 7.11% was obtained when SCPDT-PDI 4 was used as the acceptor and poly [4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b;4,5-b']dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4b]thiophene-)-2-carboxylate-2-6-diyl)](PTB7-Th) was used as the donor.The chemical structures of SCPDT-PDI 4 and PTB7-Tha re shown in Figure 1a. [21][22][23][24] It has al arge p-conjugated molecular structure, strong light-absorption property,h igh electron mobility,a nd good chemical and optical stability.…”

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confidence: 99%

“…Materials based on SCPDT have been widely used in field-effect transistors, [30] dyesensitized solar cells, [31] andp erovskite solar cells. Materials based on SCPDT have been widely used in field-effect transistors, [30] dyesensitized solar cells, [31] andp erovskite solar cells.…”

mentioning

confidence: 99%

“…Materials based on SCPDT have been widely used in field-effect transistors, [30] dyesensitized solar cells, [31] andp erovskite solar cells. [30] Due to the well-conjugated structure and electron-rich property of two cyclopenta[2,1-b;3,4-b']dithiophene(CPDTs), [34] SCPDTbased molecules are expected to show strong intramolecular charge-transfer characteristics and thus broad low-energyo ptical transitionsa nd good charge mobility.U sing the simple solution spin-coating fabrication process, ah igh PCE of 7.11% was obtained when SCPDT-PDI 4 was used as the acceptor and poly [4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b;4,5-b']dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4b]thiophene-)-2-carboxylate-2-6-diyl)](PTB7-Th) was used as the donor. SCPDT,anew spiro core with thiophenea sacentral aromatic system, shows an orthogonal molecular structure.…”

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confidence: 99%

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High‐Performance Organic Solar Cells Based on a Non‐Fullerene Acceptor with a Spiro Core

Sun

Zhang

et al. 2017

Chemistry An Asian Journal

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Derived from perylenediimide (PDI) building blocks, 3D PDI molecules are considered as a type of promising structure to overcome molecular aggregation, thus improving the performance of organic solar cells. Herein, we report a novel PDI-based derivative, SCPDT-PDI , with four PDI units connected to a unique spiro core. Attributed to this novel molecular design, SCPDT-PDI exhibits a rigid 3D structure, in which the aggregation tendency of PDI chromophores could be effectively attenuated. Additionally, strong intramolecular charge transfer and high charge mobility are achieved due to the well-conjugated structure and electron-rich property of SCPDT. Therefore, fullerene-free organic solar cells based on SCPDT-PDI and PTB7-Th achieve a remarkable high efficiency of 7.11 %. Such an excellent result demonstrates the opportunity of SCPDT to be a promising building block for non-fullerene acceptors.

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Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting Panel

Liu

Dong

Jiang

et al. 2014

Adv Funct Materials

150

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1wileyonlinelibrary.com power effi ciency (PE) >50 lm W −1 and low effi ciency roll-off at 5000 cd m −2 are still rare. [ 5 ] Considering the pursuit of various blue emitters is still ongoing, [ 6 ] it is also necessary to develop new host materials to test different kinds of emitting phosphors. Furthermore, another main application for blue hosts is for the high-effi ciency white light emission; their performances on large-size lighting panels are fascinating but still a blank in recent literature reports. [ 6 ] Therefore, constant efforts should be devoted to developing good host materials that can achieve high efficiency and fl at effi ciency roll-off simultaneously in blue/white PHOLEDs.The compounds with spiro-core are good candidates in constructing bipolar materials for the inherent orthogonal structure of two molecular halves. In addition, this approach can also effi ciently suppress intermolecular interaction by their adamant backbone, resulting in better solubility and cause entanglement in the amorphous state, then hinder recrystallization. [ 7 ] The development of spiro host material, however, is relatively slower as compared with other series of host materials. In 2005, the fi rst example of spiro host materials named SSS based on 9,9′-spirobifl uorene core is reported, which obtained EQE of ≈10% for red phosphorescence. [ 8 ] In 2008, the fi rst spiro bipolar molecule D2ACN integrated with electron-rich diphenylamine and electron-defi cient nitrile is prepared, but the EQE is just slightly improved to 10.8% with PE of 13 lm W −1 as red host material. [ 9 ] To date, there are just several attempts on blue hosts based on spiro-structure and the device performances are moderate. [ 10 ] Recently, we reported a blue host material SSTF based on new STF core, which could achieved a PE of 41.5 lm W −1 and an EQE of 18.7%. [ 11 ] In the STF molecular structure, a triphenylamine moiety is placed in vertical confi guration to fl uorene. This confi guration endows good hole-transporting ability to STF and makes it unnecessary to introduce any other arylamine groups on spiro backbone that always reduces the triplet energy (such as D2ACN). On the other hand, the fl uorene moiety can be further modifi ed by appending electron-deficient groups to enhance bipolar property. Herein, we design and prepare a new spiro host material POSTF by appending phosphine oxide group on the fl uorene moiety. It demonstrates very high EQE and extremely low effi ciency roll-offs for sky-blue (small size) and white (large size) phosphorescent devices. Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting PanelLei Ding , Shou-Cheng Dong , Zuo-Quan Jiang , * Hua Chen , and Liang-Sheng Liao * High-effi ciency blue phosphorescence devices with external quantum effi ciencies above 25% are developed using a new bipolar host material, diphenyl(10-phenyl-10 H -spiro[acridine-9,9′-fl uoren]-2′-yl)phosphine oxide (POSTF), which is constructed in orthogonal molecular structure with a ...

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4,4′‐Spirobi[cyclopenta[2,1‐b;3,4‐b′]dithiophene: A New Generation of Heterocyclic Spiro‐Type Molecules

Cited by 30 publications

References 28 publications

Violet‐to‐Blue Tunable Emission of Aryl‐Substituted Dispirofluorene–Indenofluorene Isomers by Conformationally‐Controllable Intramolecular Excimer Formation

Violet‐to‐Blue Tunable Emission of Aryl‐Substituted Dispirofluorene–Indenofluorene Isomers by Conformationally‐Controllable Intramolecular Excimer Formation

High‐Performance Organic Solar Cells Based on a Non‐Fullerene Acceptor with a Spiro Core

Orthogonal Molecular Structure for Better Host Material in Blue Phosphorescence and Larger OLED White Lighting Panel

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