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Intermolecular Hydrogen-Bond-Assisted Solid-State Dual-Emission Molecules with Mechanical Force-Induced Enhanced Emission
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-21 , DOI: 10.1021/acs.joc.2c00617 Xiaohui Wang 1 , Jianyu Zhang 2 , Xiaoyu Mao 1 , Yiwei Liu 1 , Ruikuan Li 1 , Jie Bai 1 , Jun Zhang 3 , Carl Redshaw 4 , Xing Feng 1, 5 , Ben Zhong Tang 6
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-21 , DOI: 10.1021/acs.joc.2c00617 Xiaohui Wang 1 , Jianyu Zhang 2 , Xiaoyu Mao 1 , Yiwei Liu 1 , Ruikuan Li 1 , Jie Bai 1 , Jun Zhang 3 , Carl Redshaw 4 , Xing Feng 1, 5 , Ben Zhong Tang 6
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Hydrogen bonds not only play a crucial role in the life sciences but also endow molecules with fantastic physical and chemical properties, which help in the realization of their high-tech applications. This work presents an efficient strategy for achieving highly efficient solid-state dual-emission blue emitters with mechanical force-induced enhanced emission properties via intermolecular hydrogen bonds via novel pyrene-based intermediates, namely, 1,3,6,8-tetrabromo-2,7-dihydroxypyrene (1) and 1,3,6,8-tetrabromo-2-hydroxypyrene (2), prepared via hydroxylation and bromination of pyrene in high yields. Moreover, further use of a classical Pd-catalyzed coupling reaction affords new pyrene-based luminescent materials 3–5, which display high thermal stability (in range of 336–447 °C), blue emission (<463 nm), and high quantum yields in solution. Interestingly, with the monosubstituted hydroxyl (OH) or methoxy (OMe) group located at position 2 of pyrene, compounds 4a and 5 display exciting dual emission with mechanical force-induced enhanced emission properties, due to the presence of several hydrogen-bond interactions. Moreover, this series of compounds exhibits numerous advantages, for example, deeper blue emission with a narrower full width at half-maximum, a stronger steric effect, and higher hydrophilicity. Thus, these novel bromopyrene intermediates and related pyrene-based luminescent materials will pave the way for further exploration of novel organic solid-state luminescent materials for potential application in organic electronics, bioimaging, chemosensors, etc.
中文翻译：
具有机械力诱导增强发射的分子间氢键辅助固态双发射分子
氢键不仅在生命科学中发挥着至关重要的作用，而且赋予分子奇妙的物理和化学性质，有助于实现其高科技应用。这项工作提出了一种有效的策略，通过新型芘基中间体，即 1,3,6,8-tetrabromo-2，通过分子间氢键实现具有机械力诱导增强的发射特性的高效固态双发射蓝色发射器,7-二羟基芘 ( 1 ) 和 1,3,6,8-四溴-2-羟基芘 ( 2 )，通过芘的羟基化和溴化以高收率制备。此外，进一步使用经典的 Pd 催化偶联反应可提供新的芘基发光材料3-5，其在溶液中显示出高热稳定性（在 336-447 °C 范围内）、蓝色发射（<463 nm）和高量子产率。有趣的是，单取代羟基 (OH) 或甲氧基 (OMe) 位于芘的 2 位，化合物4a和5由于存在几种氢键相互作用，因此显示出具有机械力诱导增强的发射特性的令人兴奋的双重发射。此外，这一系列化合物具有许多优点，例如更深的蓝色发射、更窄的半峰全宽、更强的空间效应和更高的亲水性。因此，这些新型溴芘中间体和相关的芘基发光材料将为进一步探索新型有机固态发光材料在有机电子、生物成像、化学传感器等方面的潜在应用铺平道路。
更新日期：2022-06-21
中文翻译：
具有机械力诱导增强发射的分子间氢键辅助固态双发射分子
氢键不仅在生命科学中发挥着至关重要的作用，而且赋予分子奇妙的物理和化学性质，有助于实现其高科技应用。这项工作提出了一种有效的策略，通过新型芘基中间体，即 1,3,6,8-tetrabromo-2，通过分子间氢键实现具有机械力诱导增强的发射特性的高效固态双发射蓝色发射器,7-二羟基芘 ( 1 ) 和 1,3,6,8-四溴-2-羟基芘 ( 2 )，通过芘的羟基化和溴化以高收率制备。此外，进一步使用经典的 Pd 催化偶联反应可提供新的芘基发光材料3-5，其在溶液中显示出高热稳定性（在 336-447 °C 范围内）、蓝色发射（<463 nm）和高量子产率。有趣的是，单取代羟基 (OH) 或甲氧基 (OMe) 位于芘的 2 位，化合物4a和5由于存在几种氢键相互作用，因此显示出具有机械力诱导增强的发射特性的令人兴奋的双重发射。此外，这一系列化合物具有许多优点，例如更深的蓝色发射、更窄的半峰全宽、更强的空间效应和更高的亲水性。因此，这些新型溴芘中间体和相关的芘基发光材料将为进一步探索新型有机固态发光材料在有机电子、生物成像、化学传感器等方面的潜在应用铺平道路。
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