Jumping Crystals of Pyrene Tweezers: Crystal-to-Crystal Transition Involving π/π-to-CH/π Assembly Mode Switching.

作者: Yoshiki Shibuya , Yoshimitsu Itoh , Takuzo Aida

DOI: 10.1002/ASIA.201700083

关键词:

摘要: Crystals of pyrene tweezers 1 with interdigitating pyrenyl blades jump vigorously at around 160 °C. Single-crystal X-ray diffraction analysis before jumping revealed the presence a "pyrene tetrad" in crystal lattice, where four are π-stacked on top each other. Upon heating to induce event, inner two probably rotate switch off their π-stacking interaction neighboring outer and form new CH-π bonds. Different from reported salient crystals, our jumps release CHCl3 as inclusion solvent.

参考文章(41)
Christopher A. Hunter, Jeremy K. M. Sanders, The nature of .pi.-.pi. interactions Journal of the American Chemical Society. ,vol. 112, pp. 5525- 5534 ,(1990) , 10.1021/JA00170A016
Steven C. Zimmerman, Milan Mrksich, Monica Baloga, Highly efficient complexation of a π-acceptor by a molecular tweezer containing two π-donors: the role of preorganization Journal of the American Chemical Society. ,vol. 111, pp. 8528- 8530 ,(1989) , 10.1021/JA00204A041
Han Wu, Nik Reeves-McLaren, Jan Pokorny, Jack Yarwood, Anthony R. West, Polymorphism, Phase Transitions, and Thermal Stability of l-Pyroglutamic Acid Crystal Growth & Design. ,vol. 10, pp. 3141- 3148 ,(2010) , 10.1021/CG100260F
Howon Lee, Chunguang Xia, Nicholas X Fang, None, First jump of microgel; actuation speed enhancement by elastic instability Soft Matter. ,vol. 6, pp. 4342- 4345 ,(2010) , 10.1039/C0SM00092B
Željko Skoko, Sharona Zamir, Panče Naumov, Joel Bernstein, The Thermosalient Phenomenon. “Jumping Crystals” and Crystal Chemistry of the Anticholinergic Agent Oxitropium Bromide Journal of the American Chemical Society. ,vol. 132, pp. 14191- 14202 ,(2010) , 10.1021/JA105508B
Toshinobu Korenaga, Yusuke Kawauchi, Takahiro Kosaki, Tadashi Ema, Takashi Sakai, Synthesis of a Molecular Tweezer Containing Pentafluorophenyl Groups and Investigation of the π–π Stacking Interaction for a Pentafluorophenyl Group in a Polar Organic Solvent Bulletin of the Chemical Society of Japan. ,vol. 78, pp. 2175- 2179 ,(2005) , 10.1246/BCSJ.78.2175
Steven C. Zimmerman, Craig M. VanZyl, Gregory S. Hamilton, Rigid molecular tweezers: preorganized hosts for electron donor-acceptor complexation in organic solvents Journal of the American Chemical Society. ,vol. 111, pp. 1373- 1381 ,(1989) , 10.1021/JA00186A035
Raghavender Medishetty, Ahmad Husain, Zhaozhi Bai, Tomče Runčevski, Robert E. Dinnebier, Panče Naumov, Jagadese J. Vittal, Single Crystals Popping Under UV Light: A Photosalient Effect Triggered by a [2+2] Cycloaddition Reaction† Angewandte Chemie. ,vol. 53, pp. 5907- 5911 ,(2014) , 10.1002/ANIE.201402040
Panče Naumov, Janusz Kowalik, Kyril M. Solntsev, Anthony Baldridge, Jong-Seok Moon, Christine Kranz, Laren M. Tolbert, Topochemistry and Photomechanical Effects in Crystals of Green Fluorescent Protein-like Chromophores: Effects of Hydrogen Bonding and Crystal Packing Journal of the American Chemical Society. ,vol. 132, pp. 5845- 5857 ,(2010) , 10.1021/JA100844M