Charge Carrier Mobility of Phenothiazine Functionalized TCBD Derivatives of Naphthalimide.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-07-21 DOI:10.1002/asia.202500259

Nikhil Ji Tiwari, Tarun, Upendra Kumar Pandey, Rajneesh Misra

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引用次数: 0

Abstract

A set of naphthalimide functionalized push-pull chromophores NPI 1-3 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling followed by [2 + 2] cycloaddition-electrocyclic ring-opening reaction. The 1,8-naphthalimide (NPI) and 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) moiety acts as an acceptor unit, whereas phenothiazine (PTZ) unit acts as a donor unit. Their photophysical, electrochemical properties, and charge carrier mobilities were investigated. Density functional theory (DFT) and TD-DFT calculations were performed on NPI 1-3 to analyze the molecular geometry, frontier molecular orbitals, molecular electrostatic potentials (MEPs), and electronic transitions related to their absorption spectra. The incorporation of cyano-based strong electron acceptor TCBD in the phenothiazine functionalized naphthalimide derivatives NPI1 resulted in TCBD incorporated chromophore NPI 2-3 which exhibits red-shifted electronic absorption spectra in the near IR region. The electrochemical properties reveal that the naphthalimide derivatives NPI 1-3 exhibit multiple redox waves, attributed to the presence of NPI and TCBD acceptor units and phenothiazine donor units. The measured hole and electron mobilities for NPI 1-3 are 4.06 × 10^-3 and 3.16 × 10^-3 cm² V^-1 s^-1, 7.5 × 10^-3 and 4.48 × 10^-3 cm² V^-1 s^-1, 6.76 × 10^-3 and 3.1 × 10^-3 cm² V^-1 s^-1, respectively, obtained by space-charge limited current (SCLC) measurements.

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吩噻嗪功能化萘酰亚胺TCBD衍生物的载流子迁移率。

采用pd催化Sonogashira交叉偶联-[2 + 2]环加成-电环开环反应，设计并合成了萘酰亚胺功能化推拉发色团NPI 1-3。1,8-萘酰亚胺（NPI）和1,1,4,4-四氰丁-1,3-二烯（TCBD）部分作为受体单元，而吩噻嗪（PTZ）单元作为供体单元。研究了它们的光物理、电化学性能和载流子迁移率。利用密度泛函理论（DFT）和TD-DFT计算了NPI 1-3的分子几何结构、前沿分子轨道、分子静电势（MEPs）以及与吸收光谱相关的电子跃迁。在吩噻嗪官能化萘酰亚胺衍生物NPI1中加入氰基强电子受体TCBD，导致TCBD加入发色团NPI 2-3，在近红外区表现出红移的电子吸收光谱。电化学性质表明萘酰亚胺衍生物NPI 1-3表现出多重氧化还原波，这是由于NPI和TCBD受体单元以及吩噻嗪给体单元的存在。NPI 1-3的空穴迁移率和电子迁移率分别为4.06 × 10-3和3.16 × 10-3 cm2 V-1 s- 1,7.5 × 10-3和4.48 × 10-3 cm2 V-1 s- 1,6.76 × 10-3和3.1 × 10-3 cm2 V-1 s-1。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).