Ketocoumarin-Based Photoinitiators for High-Sensitivity Two-Photon Lithography,ACS Applied Polymer Materials

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Ketocoumarin-Based Photoinitiators for High-Sensitivity Two-Photon Lithography
ACS Applied Polymer Materials ( IF 4.4 ) Pub Date : 2023-03-20 , DOI: 10.1021/acsapm.3c00141
Jin Tang ₁ , Xiaoyi Xu ₁ , Xiaoming Shen ₂ , Cuifang Kuang _{2,

3} , Hongzheng Chen ₁ , Minmin Shi ₁ , Ning Huang _{1,

2}

Affiliation

Ketocoumarins are attractive and distinct photosensitizers due to their high molar extinction coefficients, high intersystem crossing coefficients, and high photochemical stability. As a classic commercial ketocoumarin-based two-photon initiator, 7-diethylamino-3-thenoylcoumarin (DETC) was widely used in two-photon lithography. However, the large fluorescence quantum yield and low two-photon absorption cross section value greatly limit its application in high-throughput nanofabrication. In this work, a series of DETC derivatives were developed by extending the length of the alkyl chain and integrating different donor and acceptor groups. These ketocoumarin-based initiators, namely, compounds 1–7, were designed, synthesized, and unambiguously characterized. Compared with DETC, these compounds exhibit higher molar extinction coefficient, lower fluorescence quantum yield, higher two-photon absorption cross section, and improved sensitivity in two-photon lithography. Among these molecules, compound 7 with expanded π-electron systems and structures with enhanced intramolecular charge transfer exhibits the best sensitivity in two-photon lithography. With compound 7-based photoresist, many kinds of complex three-dimensional patterns can be fabricated using two-photon lithography at a writing speed of up to 60 mm s^–1. The high two-photon initiation sensitivity makes these compounds promising candidates for commercialization and provides a new design concept for the development of new initiators.

中文翻译：

用于高灵敏度双光子光刻的基于酮香豆素的光引发剂

由于其高摩尔消光系数、高系统间交叉系数和高光化学稳定性，酮香豆素是有吸引力且独特的光敏剂。7-二乙氨基-3-噻吩酰香豆素（DETC）作为一种经典的商业化香豆素酮基双光子引发剂，被广泛应用于双光子光刻中。然而，大的荧光量子产率和低的双光子吸收截面值极大地限制了其在高通量纳米加工中的应用。在这项工作中，通过延长烷基链的长度并整合不同的供体和受体基团，开发了一系列 DETC 衍生物。这些基于酮香豆素的引发剂，即化合物1 – 7, 被设计、合成并明确表征。与 DETC 相比，这些化合物具有更高的摩尔消光系数、更低的荧光量子产率、更高的双光子吸收截面以及双光子光刻灵敏度的提高。在这些分子中，化合物7具有扩展的 π 电子系统和增强分子内电荷转移的结构，在双光子光刻中表现出最佳灵敏度。使用基于化合物7的光刻胶，可以使用双光子光刻技术以高达 60 mm s ^–1的写入速度制造多种复杂的三维图案. 高双光子引发灵敏度使这些化合物成为商业化的有前途的候选者，并为新型引发剂的开发提供了新的设计理念。

更新日期：2023-03-20

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