2017
DOI: 10.1002/adom.201601033
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Dibenzoindigo: A Nature‐Inspired Biocompatible Semiconductor Material for Sustainable Organic Electronics

Abstract: Synthesis and systematic investigation of dibenzoindigo, a derivative of the natural colorant indigo with an extended π‐electron conjugated system, is presented. This material shows comparable hole mobilities in organic field‐effect transistors (OFETs) with the benchmark semiconductors such as pentacene and dinaphthothienothiophene. Relatively easy synthesis of dibenzoindigo, low toxicity, and excellent ambient stability in OFETs makes it promising material for designing sustainable and biocompatible organic e… Show more

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Cited by 13 publications
(8 citation statements)
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References 29 publications
(24 reference statements)
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“…While all naturally occurring indigos, according to published reports, pack with the “criss‐cross” lattice with each molecule forming single hydrogen bonds to four neighbors, some synthetic indigos such as 6,6′‐dichloroindigo and 6,6′‐dithienylindigo form linear hydrogen‐bonded chains and an idealized brick‐wall lattice (Figure c) . The extended dibenzoindigo likewise forms hydrogen‐bonded chains with a staircase pattern, reminiscent of hydrogen‐bonded pigment quinacridone . An isomer of indigo, epindolidione, can be formed by thermal isomerization of indigo at 460 °C.…”
Section: Biomolecular Electronic Materials At the Macroscalementioning
confidence: 99%
“…While all naturally occurring indigos, according to published reports, pack with the “criss‐cross” lattice with each molecule forming single hydrogen bonds to four neighbors, some synthetic indigos such as 6,6′‐dichloroindigo and 6,6′‐dithienylindigo form linear hydrogen‐bonded chains and an idealized brick‐wall lattice (Figure c) . The extended dibenzoindigo likewise forms hydrogen‐bonded chains with a staircase pattern, reminiscent of hydrogen‐bonded pigment quinacridone . An isomer of indigo, epindolidione, can be formed by thermal isomerization of indigo at 460 °C.…”
Section: Biomolecular Electronic Materials At the Macroscalementioning
confidence: 99%
“…Thermally evaporated poly(ethylene) (PE) and solution-coated poly(styrene) (PS), cross-linked benzocyclobutene derivative (BCB), shellac, or tetracontane (TC) were used for such purpose following the previously reported procedures. 24 The device architecture is completed by deposition of top silver source-drain electrodes. The detailed procedure is given in the experimental section and ESI.…”
Section: Resultsmentioning
confidence: 99%
“…It is also worthy to note that some of the vat dyes have already been used to fabricate flexible OFETs demonstrating decent electrical and mechanical performance. [18][19][20]24…”
Section: Summary Of the Biological Effectsmentioning
confidence: 99%
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“…[16][17][18][19] The third approach is based on using photochromic or other types of light-sensitive materials to enable optical switching of the devices between different electric states. 3,20,21 Different families of photochromic compounds, such as spiropyranes, [22][23][24][25][26] spirooxazines, [27][28][29] and dihetarylethenes, [30][31][32][33][34][35][36][37] have been explored as promising materials for light-triggered OFET-based memory devices. It should be emphasized that the best results were obtained when photochromic materials were placed between semiconductor and dielectric layers since the properties of this interface control the flow of charges in the transistor channel.…”
Section: Introductionmentioning
confidence: 99%