2011
DOI: 10.1002/anie.201104797
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Electron‐Accepting 6,12‐Diethynylindeno[1,2‐b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties

Abstract: Polycyclic hydrocarbons that possess extended p conjugation are of significant interest because of their potential use in optical and electronic devices such as light emitting devices, field-effect transistors, and photovoltaics.[1] While a majority of studies have focused on acenes such as pentacene and its derivatives (e.g., 1; Scheme 1), [2] these systems are susceptible to oxidative and photolytic degradation; [3] thus, there is a need for alternative, acene-like molecules. One avenue in this search has e… Show more

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Cited by 166 publications
(127 citation statements)
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“…Very recently, our group 9 and others 10 have begun to examine the isomers of indenofluorenes 11 (IFs, Fig. 2) as potential n-type materials due to their ability to reversibly accept two electrons.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Very recently, our group 9 and others 10 have begun to examine the isomers of indenofluorenes 11 (IFs, Fig. 2) as potential n-type materials due to their ability to reversibly accept two electrons.…”
Section: Introductionmentioning
confidence: 99%
“…Our initial studies showed that a range of electron-rich and electron-poor groups at the 2 and 8 positions of the indeno[1,2- b ]fluorene skeleton (e.g., 3a ) 9b had only a modest effect on the electronic properties of these compounds; however, we demonstrated subsequently that functionalizing the [1,2- b ]IFs with aryl groups at the 6 and 12 positions ( 3b ) 9c resulted in much greater variability in the redox properties of the molecules, with some displaying amphoteric behaviour. Tobe and our group reported, respectively, that [2,1- a ] isomer 4 10a and previously unknown [2,1- c ] isomer 5 9d also possessed excellent electrochemical properties with smaller HOMO-LUMO gaps than the [1,2- b ]IFs. Tobe et al very recently described unknown [2,1- b ] isomer 6 ; 10c however, the instability of the molecule may preclude its use in organic electronics.…”
Section: Introductionmentioning
confidence: 99%
“…Based on these values, the HOMO-LUMO energy gap of 2 is calculated to be 1.23 eV. Interestingly, these E HOMO and E LUMO values are significantly different from those of IF(Me)-TA ( E HOMO  = −5.84 eV and E LUMO  = −3.99 eV) 30 . In order to understand the origin of this phenomenon, density functional theory (DFT) calculations of 2(H), IF, and BDA at the B3LYP/6-311 + G(d, p) level were performed.…”
Section: Resultsmentioning
confidence: 92%
“…For this study were considered the anti-aromatic compounds; pentalene (1) [10,11,23], s-indacene (2) [10,23], indeno[1,2-b]fluorene (3) [7,24] and benzo[g]benzo [6,7]indeno[1,2-b]fluorene (4). Figure 2 shows how the frontier molecular orbital energies for these anti-aromatic molecules behave.…”
Section: Study Of the Extension Of The Anti-aromatic Systemmentioning
confidence: 99%