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Photomodulation of Two-Dimensional Self-Assembly of Azobenzene–Hexa-peri-hexabenzocoronene–Azobenzene Triads
Chemistry of Materials ( IF 7.2 ) Pub Date : 2019-06-12 00:00:00 , DOI: 10.1021/acs.chemmater.9b01535 Ian Cheng-Yi Hou 1 , Valentin Diez-Cabanes 2 , Agostino Galanti 3 , Michal Valášek 4 , Marcel Mayor 4, 5 , Jérôme Cornil 2 , Akimitsu Narita 1, 6 , Paolo Samorì 3 , Klaus Müllen 1, 7
Chemistry of Materials ( IF 7.2 ) Pub Date : 2019-06-12 00:00:00 , DOI: 10.1021/acs.chemmater.9b01535 Ian Cheng-Yi Hou 1 , Valentin Diez-Cabanes 2 , Agostino Galanti 3 , Michal Valášek 4 , Marcel Mayor 4, 5 , Jérôme Cornil 2 , Akimitsu Narita 1, 6 , Paolo Samorì 3 , Klaus Müllen 1, 7
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Achieving exquisite control over self-assembly of functional polycyclic aromatic hydrocarbons (PAH) and nanographene (NG) is essential for their exploitation as active elements in (nano)technological applications. In the framework of our effort to leverage their functional complexity, we designed and synthesized two hexa-peri-hexabenzocoronene (HBC) triads, pAHA and oAHA, decorated with two light-responsive azobenzene moieties at the pseudo-para and ortho positions, respectively. Their photoisomerization in solution is demonstrated by UV–vis absorption. 1H NMR measurements of oAHA suggested 23% of Z-form can be obtained at a photostationary state with UV irradiation (366 nm). Scanning tunneling microscopy imaging revealed that the self-assembly of pAHA and oAHA at the solid–liquid interface between highly oriented pyrolytic graphite (HOPG) and their solution in 1,2,4-trichlorobenzene can be modulated upon light irradiation. This is in contrast to our previous work using HBC bearing a single azobenzene moiety, which did not show such photomodulation of the self-assembled structure. Upon E-Z isomerization both pAHA and oAHA displayed an increased packing density on the surface of graphite. Moreover, pAHA revealed a change of self-assembled pattern from an oblique unit cell to a dimer row rectangular crystal lattice whereas the assembly of oAHA retained a dimer row structure before and after light irradiation, yet with a modification of the inter-row molecular orientation. Molecular mechanics/molecular dynamics simulations validated the self-assembly patterns of pAHA and oAHA, comprising azobenzenes in their Z-forms. These results pave the way toward use of suitably functionalized large PAHs, as well as NGs, to develop photoswitchable devices.
中文翻译：
偶氮苯-六-邻-六苯并并戊基-偶氮苯三联体的二维自组装的光调制
对功能性多环芳烃（PAH）和纳米石墨烯（NG）的自组装进行精确控制对于将其用作（纳米）技术应用中的活性元素至关重要。在我们的努力，以充分利用其功能复杂的框架，我们设计并合成了两个六围-hexabenzocoronene（HBC）黑社会，p AHA和Ø AHA，有两个光响应偶氮苯部分装饰的伪对和邻位，分别。它们在溶液中的光异构化通过紫外可见吸收证明。o AHA的1 H NMR测定表明Z的23％可以在紫外光（366 nm）的光固定状态下获得α-型。扫描隧道显微镜成像显示，p AHA和o AHA在高度定向的热解石墨（HOPG）与它们在1,2,4-三氯苯中的溶液之间的固液界面处的自组装可通过光照射进行调节。这与我们以前使用带有单个偶氮苯部分的HBC的工作相反，后者没有显示出这种自组装结构的光调制。当EZ异构化二者p AHA和ö AHA显示石墨的表面上的增加的填充密度。此外，p AHA揭示了自组装模式从斜晶胞到二聚体行矩形晶格的变化，而o AHA的组装在光照射之前和之后保持了二聚体行结构，但行间分子取向发生了改变。分子力学/分子动力学模拟验证了p AHA和o AHA的自组装模式，其中包括Z形的偶氮苯。这些结果为使用功能适当的大型PAH和NG铺平了道路，从而开发出了可光开关器件。
更新日期：2019-06-12
中文翻译：
偶氮苯-六-邻-六苯并并戊基-偶氮苯三联体的二维自组装的光调制
对功能性多环芳烃（PAH）和纳米石墨烯（NG）的自组装进行精确控制对于将其用作（纳米）技术应用中的活性元素至关重要。在我们的努力，以充分利用其功能复杂的框架，我们设计并合成了两个六围-hexabenzocoronene（HBC）黑社会，p AHA和Ø AHA，有两个光响应偶氮苯部分装饰的伪对和邻位，分别。它们在溶液中的光异构化通过紫外可见吸收证明。o AHA的1 H NMR测定表明Z的23％可以在紫外光（366 nm）的光固定状态下获得α-型。扫描隧道显微镜成像显示，p AHA和o AHA在高度定向的热解石墨（HOPG）与它们在1,2,4-三氯苯中的溶液之间的固液界面处的自组装可通过光照射进行调节。这与我们以前使用带有单个偶氮苯部分的HBC的工作相反，后者没有显示出这种自组装结构的光调制。当EZ异构化二者p AHA和ö AHA显示石墨的表面上的增加的填充密度。此外，p AHA揭示了自组装模式从斜晶胞到二聚体行矩形晶格的变化，而o AHA的组装在光照射之前和之后保持了二聚体行结构，但行间分子取向发生了改变。分子力学/分子动力学模拟验证了p AHA和o AHA的自组装模式，其中包括Z形的偶氮苯。这些结果为使用功能适当的大型PAH和NG铺平了道路，从而开发出了可光开关器件。
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