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New organic 4‐(4‐methoxystyryl)‐1‐methylpyridinium crystals for nonlinear optical applications
Yun-Sang Lee,O-Pil Kwon,Woojin Yoon,Hoseop Yun,Mojca Jazbinsek4,In Cheol Yu,Fabian Rotermund,Dongwook Kim 대한화학회 2022 Bulletin of the Korean Chemical Society Vol.43 No.11
In this study, an organic nonlinear optical salt crystal, 4-(4-methoxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate (MOS-BBS), is newly reported. MOS-BBS crystals exhibit perfectly parallel molecular ordering of 4-(4-methoxystyryl)-1-methylpyridinium (MOS) cationic chromophores with noncentrosymmetric P1space group symmetry, which provides an optimal configuration for maximizing themacroscopic second-order optical nonlinearity. The macroscopic optical nonlinearityof the MOS-BBS crystals is very large, with the diagonal effective first hyperpolarizabilityof 160 1030 esu. Furthermore, the MOS-BBS crystals exhibit a high thermalcrystal-phase stability. The lowest phase transition temperature of the MOS-BBS crystalsis 265C, which is ~90C higher than that of previously reported MOS-basedcrystals.
Kim, Pil-Joo,Jazbinsek, Mojca,Kwon, O-Pil American Chemical Society 2011 Crystal Growth & Design Vol.11 No.7
<P>We report on selective growth of highly efficient nonlinear optical stilbazolium crystals by using sequential crystal growth in different solvent systems. Stilbazolium-salt crystals DSTMS (<I>N,N</I>-dimethylamino-<I>N</I>′-methylstilbazolium 2,4,6-trimethylbenzenesulfonate) with state-of-the-art nonlinear optical properties exhibit a thin plate-like morphology when grown in methanol and a thick trapezoidal-like morphology when grown in acetonitrile. We demonstrate morphology and thickness control of bulk DSTMS crystals by using sequential crystal growth by choosing a different solvent for growing bulk crystals as for growing seed crystals. For crystals growing in methanol solution from trapezoidal-like seed crystals grown in acetonitrile solution, the average growth rate is similar as in methanol alone, but the specific growth rate is considerably different: the aspect ratio of such crystals may be 1 order of magnitude larger than for crystals growing in methanol alone. For crystals growing in acetonitrile solution from thin plate-like seed crystals grown in methanol solution, the thickness slowly increases, while the lateral size remains similar. Such morphology and thickness control of DSTMS by sequential crystal growth in different solvents is a promising technique for practical applications, where crystals of a certain thickness are desired, for example, for THz-wave generation, frequency conversion, electro-optics, and field detection.</P><P>Selective growth of the highly efficient nonlinear optical stilbazolium DSTMS (<I>N,N</I>-dimethylamino-<I>N</I>′-methylstilbazolium 2,4,6-trimethylbenzenesulfonate) crystals is successfully demonstrated by using sequential crystal growth in different solvent systems, which is a promising technique for practical applications including THz wave applications.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/cgdefu/2011/cgdefu.2011.11.issue-7/cg200329m/production/images/medium/cg-2011-00329m_0005.gif'></P>
Seo, Ji-Youn,Jazbinsek, Mojca,Choi, Eun-Young,Lee, Seung-Heon,Yun, Hoseop,Kim, Jong-Taek,Lee, Yoon Sup,Kwon, O-Pil American Chemical Society 2013 Crystal Growth & Design Vol.13 No.3
<P>We report a series of π-conjugated phenyltriene analogous molecules and crystals having different thiolated building blocks, which significantly influence the molecular ordering in the crystalline state. Whereas a polyene crystal having the methylthiolated phenyl (SM) building block exhibits a zigzag molecular ordering based on head-to-tail hydrogen bonds, the crystals of other analogues having the biphenyl sulfane (SB) block exhibit isomorphic crystal structures with herringbone packing. In one of these isomorphic crystals having both SM and SB building blocks, the herringbone packing is accompanied with head-to-tail hydrogen bonds. As a result of such packing promoted by SM and SB building blocks, the rigid phenyltriene bridge shows an unusual twisting and bending conformation, which is accompanied with a significant change of physical properties, such as fluorescent, linear, and nonlinear optical properties in the solid state.</P><P>We report a series of π-conjugated phenyltriene analogous molecules and crystals having different thiolated building blocks. In one of these isomorphic crystals having both methylthiolated phenyl (SM) and biphenyl sulfane (SB) building blocks, the rigid phenyltriene bridge shows an unusual twisting and bending conformation.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/cgdefu/2013/cgdefu.2013.13.issue-3/cg301625d/production/images/medium/cg-2012-01625d_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cg301625d'>ACS Electronic Supporting Info</A></P>
Kim, Jongtaek,Kwon, O-Pil,Jazbinsek, Mojca,Park, Young Choon,Lee, Yoon Sup American Chemical Society 2015 JOURNAL OF PHYSICAL CHEMISTRY C - Vol.119 No.22
<P>Terahertz absorption of organic materials is closely linked to molecular arrangements and their intermolecular interactions and is important for material identification as well as THz generation. Theoretical calculations of solid-state vibrations known as phonons help to understand intermolecular interactions responsible for THz absorption but frequently are of limited use without considering dispersion interaction. In this study, we have calculated the THz phonon modes of an organic model crystal 2,2′-bithiophene, considering dispersion intermolecular interactions assuming the fixed cell dimensions. Both energies and intensities of phonon modes at low frequencies were interpreted concentrating on the intermolecular level in conjunction with hydrogen bonds and showed an excellent agreement with the experimental results. This approach to identify the phonon modes responsible for strong THz absorptions and to interpret those modes in terms of intermolecular vibrations is also expected to be applicable to the field of THz generation using nonlinear optical organic crystals.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jpccck/2015/jpccck.2015.119.issue-22/acs.jpcc.5b02661/production/images/medium/jp-2015-02661n_0005.gif'></P>