Push–Pull Heptamethines Near the Cyanine Limit Exhibiting Large Quadratic Electro-Optic Effect

Weilong Chen; Taili Liu; Jie Zou; Di Zhang; Man Kit Tse; Sai-Wing Tsang; Jingdong Luo; Alex K-Y. Jen

doi:10.1002/adma.202306089

Push–Pull Heptamethines Near the Cyanine Limit Exhibiting Large Quadratic Electro-Optic Effect

Weilong Chen (Co-first Author), Taili Liu (Co-first Author), Jie Zou, Di Zhang, Man Kit Tse, Sai-Wing Tsang^*, Jingdong Luo^*, Alex K-Y. Jen^*

^*Corresponding author for this work

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

9 Citations (Scopus)

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Abstract

Harnessing the quadratic electro-optic (QEO) of near-infrared polymethine chromophores over broad telecom wavelength bands is a subject of immense potential but remains largely under-investigated. Herein a series of push–pull heptamethines containing the tricyanofuran (TCF) acceptors and indoline or benzo[e]indoline donors are reported. These dipolar chromophores can attain a highly delocalized “cyanine-like” electronic ground state in solvents spanning a wide range of polarities, in some cases even closer to the ideal polymethine state than symmetrical cyanines. A transmission-mode electromodulation spectroscopy is used to study the electric-field-induced changes in optical absorption and refraction of polymer films doped with heptamethine chromophores, and large and thermally stable QEO effect with high efficiency-loss figure-of-merits that compare favorably to those from dipolar polyenes in poled or unpoled polymers and III-V semiconductors is obtained. The study opens a path for developing organic materials based on cyanine-like merocyanines for complementary metal oxide semiconductor -compatible, fast, efficient, and low-loss electro-optic modulation. © 2023 Wiley-VCH GmbH.

Original language	English
Article number	2306089
Journal	Advanced Materials
Volume	36
Issue number	17
Online published	7 Aug 2023
DOIs	https://doi.org/10.1002/adma.202306089
Publication status	Published - 25 Apr 2024

Funding

This work was supported by Fundamental Research Project funding from GuangdongHong Kong-Macao research team projects of Guangdong Basic and Applied Basic Research Foundation (2020B1515130006), National Natural Science Foundation of China (21975213 and U20A20165), Research Grants Council (RGC) of Hong Kong (RGC Ref No. 11306320, 11317922, and 11303721), internal research supports or initiatives from City University of Hong Kong (7005262, 9680263, and 9610454).

Research Keywords

cyanine-like
figure-of-merits
push–pull heptamethines
quadratic electro-optic
transmission-mode electromodulation

Publisher's Copyright Statement

COPYRIGHT TERMS OF DEPOSITED POSTPRINT FILE: This is the accepted version of the following article: Chen, W., Liu, T., Zou, J., Zhang, D., Tse, M. K., Tsang, S-W., Luo, J., & Jen, A. K-Y. (2024). Push–Pull Heptamethines Near the Cyanine Limit Exhibiting Large Quadratic Electro-Optic Effect. Advanced Materials, 36(17), Article 2306089
which has been published in final form at https://doi.org/10.1002/adma.202306089. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

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abstract = "Harnessing the quadratic electro-optic (QEO) of near-infrared polymethine chromophores over broad telecom wavelength bands is a subject of immense potential but remains largely under-investigated. Herein a series of push–pull heptamethines containing the tricyanofuran (TCF) acceptors and indoline or benzo[e]indoline donors are reported. These dipolar chromophores can attain a highly delocalized “cyanine-like” electronic ground state in solvents spanning a wide range of polarities, in some cases even closer to the ideal polymethine state than symmetrical cyanines. A transmission-mode electromodulation spectroscopy is used to study the electric-field-induced changes in optical absorption and refraction of polymer films doped with heptamethine chromophores, and large and thermally stable QEO effect with high efficiency-loss figure-of-merits that compare favorably to those from dipolar polyenes in poled or unpoled polymers and III-V semiconductors is obtained. The study opens a path for developing organic materials based on cyanine-like merocyanines for complementary metal oxide semiconductor -compatible, fast, efficient, and low-loss electro-optic modulation. {\textcopyright} 2023 Wiley-VCH GmbH.",

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Push–Pull Heptamethines Near the Cyanine Limit Exhibiting Large Quadratic Electro-Optic Effect

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GRF: Molecular Bandgap Engineering of Organic Electro-Optic Materials for Achieving Ultralarge Near-Resonance Optical Nonlinearities Guided by Spectroscopic Electromodulation and Ellipsometry

GRF: Efficient Pyroelectric Poling of High-Performance Organic Electro-Optic Materials for Hybrid Photonic Platforms

GRF: Ultra-Efficient Supramolecular Organic Electro-Optic Materials for Hybrid Graphene Organic Platform

Cite this

Push–Pull Heptamethines Near the Cyanine Limit Exhibiting Large Quadratic Electro-Optic Effect

Abstract

Funding

Research Keywords

Publisher's Copyright Statement

Access Output

Other Access Options

Permanent Link

Other Files and Links

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Projects

GRF: Molecular Bandgap Engineering of Organic Electro-Optic Materials for Achieving Ultralarge Near-Resonance Optical Nonlinearities Guided by Spectroscopic Electromodulation and Ellipsometry

GRF: Efficient Pyroelectric Poling of High-Performance Organic Electro-Optic Materials for Hybrid Photonic Platforms

GRF: Ultra-Efficient Supramolecular Organic Electro-Optic Materials for Hybrid Graphene Organic Platform

Cite this