Rational design of bio-inspired high-performance ambipolar organic semiconductor materials based on indigo and its derivatives

Zhang, Shou Feng; Chen, Xiankai; Fan, Jian Xun; Ren, Ai Min

doi:10.1016/j.orgel.2015.05.021

Cited by 24 publications

(12 citation statements)

References 61 publications

(63 reference statements)

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“…Among systems of natural origin, Indigo [2,2′-bis(2,3-dihydro-3-oxoindolyliden), Figure ] has been shown to be a most promising biocompatible semiconductor material, exhibiting balanced ambipolar transport in OTFTs. − Its properties in thin films were found to be strongly dependent on the surface on which the film is grown, , with hydrocarbon-based materials such as polyethylene and tetratetracontane outperforming other dielectrics. Recently, this has been attributed to a polymorphic modification, induced by the dielectric acting as a template …”

Section: Introductionmentioning

confidence: 99%

Structural, Spectroscopic, and Computational Characterization of the Concomitant Polymorphs of the Natural Semiconductor Indigo

et al. 2018

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Indigo [2,], a commonly used natural dye, has been shown to exhibit a highly promising semiconducting behavior, allowing for the realization of ambipolar devices. Nevertheless, up to date, it is still unclear which crystal structure is present in the thin films, a piece of information relevant for device applications. In this work, we address this issue by an indepth characterization of the polymorphs of Indigo in the bulk and in drop-cast films. To do this, X-ray diffraction (XRD) and micro-Raman spectroscopy have been employed jointly, with the support of state-of-the-art density functional theory calculations in the solid state. Structural and spectroscopic characterizations have established that the two known A and B polymorphs grow as concomitant in the bulk under most of the experimental conditions adopted in this work. In the drop-cast films, XRD cannot unambiguously identify the structure, but Raman spectroscopy is effective in establishing that only the B form is present. The calculations augment the experiments, providing valuable insights into the relative thermodynamic stability of the two forms as a function of temperature. They also allow for a more comprehensive characterization of the Raman modes.

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Section: Introductionmentioning

confidence: 99%

Structural, Spectroscopic, and Computational Characterization of the Concomitant Polymorphs of the Natural Semiconductor Indigo

et al. 2018

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“…Natural and bio-inspired organic conjugated materials [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ] have become a new wave. Given the sustainability, biocompatibility, non-toxicity, versatility and potentially low-cost of bio-organic bio-inspired materials, it is evident that such materials will be widely considered as candidates for future bio-organic semiconductor science and technology, such as ultra-thin electronic platforms for surgical and point-of-care devices, diagnostic implants [ 8 , 9 , 10 , 11 ], soft robotics [ 12 , 13 ], biodegradable electronics [ 14 , 15 ] and food packaging [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Riboflavin-Inspired Conjugated Bio-Organic Semiconductors

et al. 2018

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Flavins are known to be extremely versatile, thus enabling routes to innumerable modifications in order to obtain desired properties. Thus, in the present paper, the group of bio-inspired conjugated materials based on the alloxazine core is synthetized using two efficient novel synthetic approaches providing relatively high reaction yields. The comprehensive characterization of the materials, in order to evaluate the properties and application potential, has shown that the modification of the initial alloxazine core with aromatic substituents allows fine tuning of the optical bandgap, position of electronic orbitals, absorption and emission properties. Interestingly, the compounds possess multichromophoric behavior, which is assumed to be the results of an intramolecular proton transfer.

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“…The NM analyses were executed by CT modeling package which is developed by our group. 67,68 The contributions of each vibration mode to hole/electron reorganization energies (λ h /λ e ) are shown in Table S3 and Figure S4. For Ant, the contributions for λ h mainly derive from the high-frequency region of C−H bending vibration (1421 cm −1 ) and CC stretching vibrations (1583 and 1683 cm −1 ).…”

Section: Theoretical Methodsmentioning

confidence: 99%

Theoretical Investigations into the Electron and Ambipolar Transport Properties of Anthracene-Based Derivatives

Qin

Fan

et al. 2019

J. Phys. Chem. A

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To obtain anthracene-based derivatives with electron transport behavior, two series of anthracene-based derivatives modified by trifluoromethyl groups (−CF3) and cyano groups (−CN) at the 9,10-positions of the anthracene core were studied. Their electronic structures and crystal packings were also analyzed and compared. The charge-carrier mobilities were evaluated by quantum nuclear tunneling theory based on the incoherent charge-hopping model. Our results suggest that introducing −CN groups at 9,10-positions of the anthracene core is more favorable than introducing −CF3 to maintain great planar rigidity of the anthracene skeleton, decreasing more lowest unoccupied molecular orbital energy levels (0.45–0.55 eV), reducing reorganization energies, and especially forming a tight packing motif. Eventually, the excellent electron transport materials could be obtained. The molecule 1-B in Series 1 containing −CF3 groups is an ambipolar organic semiconductor (OSC) material with a 2D transport network, and its value of μh‑max/μe‑max is 1.75/0.47 cm2 V–1 s–1 along different directions; 2-A and 2-C in Series 2 with −CN groups are excellent n-type OSC candidates with the maximum intrinsic mobilities of 3.74 and 2.69 cm2 V–1 s–1 along the π–π stacking direction, respectively. Besides, the Hirshfeld surface and quantum theory of atoms in molecules analyses were applied to reveal the relationship between noncovalent interactions and crystal stacking.

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Rational design of bio-inspired high-performance ambipolar organic semiconductor materials based on indigo and its derivatives

Cited by 24 publications

References 61 publications

Structural, Spectroscopic, and Computational Characterization of the Concomitant Polymorphs of the Natural Semiconductor Indigo

Structural, Spectroscopic, and Computational Characterization of the Concomitant Polymorphs of the Natural Semiconductor Indigo

Novel Riboflavin-Inspired Conjugated Bio-Organic Semiconductors

Theoretical Investigations into the Electron and Ambipolar Transport Properties of Anthracene-Based Derivatives

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