The Structure of Fluorene<sup>1</sup>

Weisburger, John H.; Weisburger, Elizabeth K.; Ray, Francis Earl

doi:10.1021/ja01165a118

Cited by 34 publications

(29 citation statements)

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“…First described by Clarkson and Gomberg in 1930, [54] it was readily obtained in a two-step synthesis from 2-iodobiphenyl and fluorenone through a metal-halogen exchange reaction. [55][56][57][58] As DSF-IF can be considered as the joining of two SBF moieties through a shared phenyl ring, it seemed reasonable to adopt a similar strategy. Our retrosynthetic approach, based on a double lithium-halogen exchange reaction, is presented in Scheme 1 and involved 2,2''-di-…”

Section: Synthesis Of Dsf-if Derivativesmentioning

confidence: 99%

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Poriel¹,

Liang²,

Rault‐Berthelot³

et al. 2007

Chemistry A European J

131

229

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A series of new dispiro[fluorene-9',6,9'',12-indeno[1,2b]fluorenes] (DSF-IFs) has been synthesised. These new building blocks for blue-light-emitting devices and electroactive polymers combine indenofluorene (IF) and spirobifluorene (SBF) properties. We report here our synthetic investigations towards these new structures and their thermal, structural, photophysical and electrochemical properties. These properties have been compared to those of IF and SBF. We also report the anodic oxidation of DSF-IFs that leads to the formation of non-soluble transparent three-dimensional polymers. The structural and electrochemical behaviour of these polymers has been studied. The first application of these building blocks as new blue-light-emitting materials in organic light-emitting diodes (OLED) is also reported.

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Section: Synthesis Of Dsf-if Derivativesmentioning

confidence: 99%

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Poriel¹,

Liang²,

Rault‐Berthelot³

et al. 2007

Chemistry A European J

131

229

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“…[13][14][15] And among a large number of polymer donors, poly(3-hexylthiophene) (P3HT) is an important candidate to produce effective and low-cost OPVs owing to high quantity available over 10 kg as well as its stablility. [18][19][20][21][22][23][24][25][26][27][28][29] Since spirofluorene (SF) was reproted in 1950, [30] quite a lot of SMAs with SF as the central core have been studied because the 3D configuration can suppress the self-aggregation very well in the film and finaly tune the blend morphology. Firstly, SMAs should have high-lying energy levels to match well with P3HT in order to decrease the potential loss and promote exciton dissociation simultaneously.…”

Section: Introductionmentioning

confidence: 99%

Wide Band Gap Non‐Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End‐Capped Groups for P3HT‐Based Organic Solar Cells

et al. 2018

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Spirofluorene (SF) and benzo [d][1,2,3]triazole (BTA) have been considered as promising building blocks to construct n-type photovoltaic materials. Herein, three new small molecule acceptors (SMAs) named BTA21, BTA23 and BTA27 with the structure of A 2 ＝A 1 -D-A 1 ＝A 2 have been designed, in which SF and BTA were used as a central unit of D and bridged acceptor unit of A 1 , respectively. In addition, 3-ethylrhodanine, 2-(3-ethyl-4oxothiazolidin-2-ylidene)malononitrile and malononitrile were chosen as terminal acceptor units to modulate the properties of the final SMAs. Three SMAs show wide optical band gaps (E g ) of 2.19, 2.15 and 2.21 eV, respectively, with gradually down-shift of the lowest unoccupied molecular orbital (LUMO) levels in the order of BTA21, BTA23 and BTA27 depending on the electron-withdrawing capability of terminal acceptor units. BTA21 shows great advantages with respect to donor poly(3-hexylthiophene) (P3HT) over BTA23 and BTA27, such as well energy-level matching, complementary absorption and proper morphology. Concequently, P3HT:BTA21 shows the best power conversion efficiency (PCE) value of 3.28% with an open-circuit voltage (V OC ) of 1.02 V, a short-circuit current (J SC ) of 5.45 mA•cm -2 and a fill factor (FF) of 0.59. These results indicate that the terminal acceptor group end-capped in SMAs plays a significant role in controlling their optical, electronic, and photovoltaic properties.Scheme 1 Synthetic routes of three small molecules BTA21, BTA23 and BTA27

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“…In contrast, recent stereochemical (Weisburger et al, 1950) and ultra-violet spectroscopic (Merkel & Wiegand, 1947, 1948) studies on fluorene and an X-ray analysis (Fenimore, 1948) of the closely related bifluorene (dibiphenylene-ethylene)molecule indicate a uniplanar structure for the fluorene carbon skeleton. Since the details of the fluorene structure are of some interest from the point of view of valence theory and chemical reactivity (Lothrop, 1939) and in relation to carcenogenicity of fluorene derivatives (Miller et al, 1949; Sandin et al, 1952) The essential correctness of the proposed planar structure of fluorene is regarded as established.…”

mentioning

confidence: 96%

On the crystal and molecular structure of fluorene

Brown¹,

Bortner²

1954

Acta Cryst

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According to the X-ray analysis of crystalline fluorene by Iball (1936), the two six-membered rings in the fluorene molecule are each tilted up about 20 ° out of the plane of the five-membered ring. In contrast, recent stereochemical (Weisburger et al., 1950) and ultra-violet spectroscopic (Merkel & Wiegand, 1947, 1948) studies on fluorene and an X-ray analysis (Fenimore, 1948) of the closely related bifluorene (dibiphenylene-ethylene)molecule indicate a uniplanar structure for the fluorene carbon skeleton. Since the details of the fluorene structure are of some interest from the point of view of valence theory and chemical reactivity (Lothrop, 1939) and in relation to carcenogenicity of fluorene derivatives (Miller et al., 1949; Sandin et al., 1952) The essential correctness of the proposed planar structure of fluorene is regarded as established. The process of refinement is being carried out, and efforts are being made to record more of the 1090 reflections theoretically accessible using Cu K~ radiation, in the hope of achieving a very accurate structure determination.

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The Structure of Fluorene¹

Cited by 34 publications

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Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Wide Band Gap Non‐Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End‐Capped Groups for P3HT‐Based Organic Solar Cells

On the crystal and molecular structure of fluorene

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The Structure of Fluorene1

Cited by 34 publications

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Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Dispirofluorene–Indenofluorene Derivatives as New Building Blocks for Blue Organic Electroluminescent Devices and Electroactive Polymers

Wide Band Gap Non‐Fullerene Small Molecular Acceptors Containing Spirobifluorene and Benzotriazole with Three Different End‐Capped Groups for P3HT‐Based Organic Solar Cells

On the crystal and molecular structure of fluorene

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The Structure of Fluorene¹