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

Shou-Feng Zhang; Xian-Kai Chen; Jian-Xun Fan; Ai-Min Ren

doi:10.1016/j.orgel.2015.05.021

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

Shou-Feng Zhang, Xian-Kai Chen, Jian-Xun Fan, Ai-Min Ren^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

27 Citations (Scopus)

Abstract

Indigoids have received much attention as the candidates of sustainable ambipolar organic semiconductor. However, the low charge carrier mobilities extremely limit their practical applications. Therefore, in-depth understanding of their electronic-structure properties and rational molecular modifications are urgently required. Here, we propose a promising strategy to design ambipolar organic semiconductors based on indigo fragments. Moreover, we predicted the organic crystal structures by evolutionary algorithm combined with DFT-D method. Charge transport properties have been significantly improved for the designed molecules, such as narrower energy gaps, higher electron affinity, larger transfer integrals as well as much smaller reorganization energies for hole and electron. Thusly, remarkable ambipolar charge transport behavior has been predicted, for example, the charge carrier mobilities are up to μ_h/μ_e = 7.71/5.42 cm² V^-1 s^-1 for NN-indigo-6,6′-2CN and μ_h/μ_e = 5.15/2.13 cm² V^-1 s^-1 for C₉-NN-indigo-6,6′-2CN respectively.

Original language	English
Pages (from-to)	12-25
Journal	Organic Electronics
Volume	24
DOIs	https://doi.org/10.1016/j.orgel.2015.05.021
Publication status	Published - 26 May 2015
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Research Keywords

Ambipolar charge transport
Crystal structure prediction
Environmentally friendly organic semiconductors
Indigoids
Marcus electron transfer theory

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

abstract = "Indigoids have received much attention as the candidates of sustainable ambipolar organic semiconductor. However, the low charge carrier mobilities extremely limit their practical applications. Therefore, in-depth understanding of their electronic-structure properties and rational molecular modifications are urgently required. Here, we propose a promising strategy to design ambipolar organic semiconductors based on indigo fragments. Moreover, we predicted the organic crystal structures by evolutionary algorithm combined with DFT-D method. Charge transport properties have been significantly improved for the designed molecules, such as narrower energy gaps, higher electron affinity, larger transfer integrals as well as much smaller reorganization energies for hole and electron. Thusly, remarkable ambipolar charge transport behavior has been predicted, for example, the charge carrier mobilities are up to μh/μe = 7.71/5.42 cm2 V-1 s-1 for NN-indigo-6,6′-2CN and μh/μe = 5.15/2.13 cm2 V-1 s-1 for C9-NN-indigo-6,6′-2CN respectively.",

keywords = "Ambipolar charge transport, Crystal structure prediction, Environmentally friendly organic semiconductors, Indigoids, Marcus electron transfer theory",

author = "Shou-Feng Zhang and Xian-Kai Chen and Jian-Xun Fan and Ai-Min Ren",

note = "Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected]. ",

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AU - Zhang, Shou-Feng

AU - Chen, Xian-Kai

AU - Fan, Jian-Xun

AU - Ren, Ai-Min

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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N2 - Indigoids have received much attention as the candidates of sustainable ambipolar organic semiconductor. However, the low charge carrier mobilities extremely limit their practical applications. Therefore, in-depth understanding of their electronic-structure properties and rational molecular modifications are urgently required. Here, we propose a promising strategy to design ambipolar organic semiconductors based on indigo fragments. Moreover, we predicted the organic crystal structures by evolutionary algorithm combined with DFT-D method. Charge transport properties have been significantly improved for the designed molecules, such as narrower energy gaps, higher electron affinity, larger transfer integrals as well as much smaller reorganization energies for hole and electron. Thusly, remarkable ambipolar charge transport behavior has been predicted, for example, the charge carrier mobilities are up to μh/μe = 7.71/5.42 cm2 V-1 s-1 for NN-indigo-6,6′-2CN and μh/μe = 5.15/2.13 cm2 V-1 s-1 for C9-NN-indigo-6,6′-2CN respectively.

AB - Indigoids have received much attention as the candidates of sustainable ambipolar organic semiconductor. However, the low charge carrier mobilities extremely limit their practical applications. Therefore, in-depth understanding of their electronic-structure properties and rational molecular modifications are urgently required. Here, we propose a promising strategy to design ambipolar organic semiconductors based on indigo fragments. Moreover, we predicted the organic crystal structures by evolutionary algorithm combined with DFT-D method. Charge transport properties have been significantly improved for the designed molecules, such as narrower energy gaps, higher electron affinity, larger transfer integrals as well as much smaller reorganization energies for hole and electron. Thusly, remarkable ambipolar charge transport behavior has been predicted, for example, the charge carrier mobilities are up to μh/μe = 7.71/5.42 cm2 V-1 s-1 for NN-indigo-6,6′-2CN and μh/μe = 5.15/2.13 cm2 V-1 s-1 for C9-NN-indigo-6,6′-2CN respectively.

KW - Ambipolar charge transport

KW - Crystal structure prediction

KW - Environmentally friendly organic semiconductors

KW - Indigoids

KW - Marcus electron transfer theory

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DO - 10.1016/j.orgel.2015.05.021

M3 - RGC 21 - Publication in refereed journal

SN - 1566-1199

VL - 24

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EP - 25

JO - Organic Electronics

JF - Organic Electronics

ER -

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

Abstract

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