Indeno[2,1‐<i>b</i>]fluorene: A 20‐π‐Electron Hydrocarbon with Very Low‐Energy Light Absorption

Shimizu, Akihiro; Kishi, Ryohei; Nakano, Masayoshi; Shiomi, Daisuke; Sato, Kazunobu; Takui, Takeji; Hisaki, Ichiro; Miyata, Mikiji; Tobe, Yoshito

doi:10.1002/anie.201302091

Cited by 240 publications

(160 citation statements)

References 43 publications

(24 reference statements)

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“…These relatively large HOMO LUMO gaps are consistent with the nonmagnetic behavior observed in the variable temperature Figure 22). 80 Biradical character indeno [2,1-b]fluorene comes to 68% on the basis of the brokensymmetry UHF calculation, and this significant biradical character affects the appearance of 1 H NMR signals of 38. At room temperature, 38 showed only broad signals, and upon cooling, progressive line sharpening was observed.…”

Section: ¹1mentioning

confidence: 99%

Recent Progress in Quinoidal Singlet Biradical Molecules

2014

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Section: ¹1mentioning

confidence: 99%

Recent Progress in Quinoidal Singlet Biradical Molecules

2014

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“…In addition, the molecular structure should be highly thermally and electrically stable in a device to allow the fabrication of a circuit. 11,12,[21][22][23][24][25][26][27][28][29][30][31] For example, due to its high triplet state energy level, the 7,12-dihydroindeno[1,2-a]fluorene isomer (anti bridged metaterphenyl) has emerged as an interesting host material for blue phosphorescent OLEDs. 3,7 has led us to focus on other molecular fragments barely investigated, i.e.…”

Section: Introductionmentioning

confidence: 99%

The structure–property relationship study of electron-deficient dihydroindeno[2,1-b]fluorene derivatives for n-type organic field effect transistors

et al. 2015

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A bridged syn triphenylene derivative, namely 5,7-dihydroindeno[2,1-b]fluorene, functionalized with dicyanovinylene units (2,1-b)-IF( Q Q QC(CN) 2 ) 2 has been designed, synthesized and characterized. Its optical and electrochemical properties have been carefully studied through a combined experimental and theoretical approach and compared to those of three other structurally related dihydro[2,1-b]indenofluorene derivatives bearing methylenes,which possesses a very low LUMO level, ca. À3.81 eV, has been successfully used as an active layer in n-channel OFETs using an epoxy based photoresist SU-8 as the gate insulator. (2,1-b)-IF(Q Q QC(CN) 2 ) 2 based n-channel OFETs show promising properties such as a low threshold voltage functioning of 7.2 V (low gate-source and drain-source voltages), a high ratio between the on and the off currents (6.3 Â 10 5 ), interesting subthreshold swing (SS = 2.16) and electron mobility (410 À3 cm 2 V À1 s À1 ) and excellent stability under electrical stress. This electrical stability has allowed the incorporation of (2,1-b)-IF(Q Q QC(CN) 2 ) 2 based n-channel OFETs in an integrated circuit. Thus, as a proof of concept, pseudo CMOS inverters made of n-type (2,1-b)-IF( Q Q QC(CN) 2 ) 2 -based OFETs have been fabricated and characterized highlighting the potential of this new family of materials.View Article Online † † It should be mentioned that the trend is perfectly followed as the LUMO of (2,1-b)-IF(Q Q QO) 2 lies at À2.49 eV. ‡ ‡ As depicted below, TD-DFT calculations have allowed assigning the low energy band in (2,1-b)-IF(Q Q QO) 2 , (2,1-b)-IF(Q Q QO)(Q Q QC(CN) 2 ) and (2,1-b)-IF(Q Q QC(CN) 2 ) 2 to an HOMO/LUMO transition.

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“…In addition, highly air sensitive benzo homolog, benz[c]indeno[2,1-a]fluorene 6b with a half-life of only 77 min under air at room temperature, was isolated and its structure and unusual reactivity owing to the biradical character elucidated [17]. Moreover, dimesityl derivative 4b of m-QDM congener 4a was synthesized and its structure and extraordinary optical property were unveiled [18]. In this article, we review the results from our laboratories regarding indenofluorenes 3b and 6b both having an o-QDM substructure and 4b with an m-QDM unit and then discuss about some personal prospects in this field.…”

Section: Indenofluorene Isomersmentioning

confidence: 99%

Indenofluorene congeners: Biradicaloids and beyond

Shimizu

Nobusue

Miyoshi

et al. 2014

Pure and Applied Chemistry

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Singlet biradicaloids are certainly one of the most frequently discussed topics at ISNA-15. In this review our own work on the synthesis, molecular structures, and physical properties relevant to biradical character of indenofluorene isomers are described. These include indeno[2,1-a]fluorene with an o-quinodimethane substructure, benz[c]indeno[2,1-a]fluorene which is the first 2,3-naphthoquinodimethane derivative isolated, and indeno[2,1-b]fluorene with an m-quinodimethane (m-xylylene) subunit. The observed physical properties are explained in terms of the theoretically derived biradical factors (y), HOMO-LUMO energy gaps, and singlettriplet energy gaps in the ground state electronic configurations. In addition, we discuss here two perspectives in the biradicaloid chemistry, (i) two-and three-dimensional indenofluorene congeners arranged in a macrocyclic form and (ii) macrocyclic indenofluorenes having multiple radical characters.

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Indeno[2,1‐b]fluorene: A 20‐π‐Electron Hydrocarbon with Very Low‐Energy Light Absorption

Cited by 240 publications

References 43 publications

Recent Progress in Quinoidal Singlet Biradical Molecules

Recent Progress in Quinoidal Singlet Biradical Molecules

The structure–property relationship study of electron-deficient dihydroindeno[2,1-b]fluorene derivatives for n-type organic field effect transistors

Indenofluorene congeners: Biradicaloids and beyond

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