Towards Optical Information Recording: A Robust Visible-Light-Driven Molecular Photoswitch with the Ring-Closure Reaction Yield Exceeding 96.3 %

被引:21
作者
Hong, Pan [1 ]
Liu, Jing [1 ]
Qin, Kai-Xuan [1 ]
Tian, Rui [1 ]
Peng, Ling-Yan [1 ]
Su, Yun-Shu [1 ]
Gan, Zongsong [1 ]
Yu, Xiang-Xiang [2 ]
Ye, Lei [2 ]
Zhu, Ming-Qiang [1 ]
Li, Chong [1 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Opt & Elect Informat, Wuhan Natl Lab Optoelect, Luoyu Rd 1037, Wuhan 430074, Peoples R China
[2] Huazhong Univ Sci & Technol, Sch Integrated Circuits, Luoyu Rd 1037, Wuhan 430074, Peoples R China
基金
中国国家自然科学基金;
关键词
Diarylethene; Information Recording; Molecular Photoswitch; Optical Storage; Visible Light; DIARYLETHENES; DESIGN; DIHETEROARYLETHENES; PHOTOCYCLIZATION; DERIVATIVES; MEMORIES; CRYSTALS;
D O I
10.1002/anie.202316706
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diarylethene molecular photoswitches hold great fascination as optical information materials due to their unique bistability and exceptional reversible photoswitching properties. Conventional diarylethenes, however, rely on UV light for ring-closure reactions, typically with modest yields. For practical application, diarylethenes driven by visible lights are preferred but achieving high ring-closure reaction yield remains a significant challenge. Herein, we synthesized a novel all-visible-light-driven photoswitch, TPAP-DTE, by facilely endcapping the dithienylethene (DTE) core with triphenylamine phenyl (TPAP) groups. Owing to the electron-donating conjugation effect of TPAP, the open-form TPAP-DTE responds strongly to short-wavelength visible lights with considerable photocyclization quantum yields and molar absorption coefficient. Upon 405 nm visible-light irradiation, TPAP-DTE achieves a ring-closure reaction yield exceeding 96.3 % (confirmed by both nuclear magnetic resonance spectroscopy and high-performance liquid chromatography). Its ring-opening reaction yield is 100 % upon irradiation with long-wavelength visible light. TPAP-DTE could be regarded as a bidirectional "quasi"-quantitative conversion molecular switch. Furthermore, TPAP-DTE exhibits robust fatigue resistance over 100 full photoswitching cycles and great anti-aging property under 85 degrees C and 85 % humidity for at least 1000 h. Consequently, its rewritable QR-code, multilevel data storage, and anti-counterfeiting/encryption applications are successfully demonstrated exclusively using visible lights, positioning TPAP-DTE as a highly promising medium for information recording.
引用
收藏
页数:11
相关论文
共 66 条
  • [1] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [2] Simple electron donor molecules based on triphenylamine and carbazole derivatives
    Belieres, M.
    Sartor, V.
    Fabre, P. -L.
    Poteau, R.
    Bordeau, G.
    Chouini-Lalanne, N.
    [J]. DYES AND PIGMENTS, 2018, 153 : 275 - 283
  • [3] Fluorescent Molecular Photoswitches for the Generation of All-Optical Encryption Keys
    Benitez-Martin, Carlos
    Rouillon, Jean
    Grotli, Morten
    Andreasson, Joakim
    [J]. CHEMPHOTOCHEM, 2023, 7 (12):
  • [4] Visible-Light-Activated Molecular Switches
    Bleger, David
    Hecht, Stefan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) : 11338 - 11349
  • [5] Two-Way Photoswitching Using One Type of Near-Infrared Light, Upconverting Nanoparticles, and Changing Only the Light Intensity
    Boyer, John-Christopher
    Carling, Carl-Johan
    Gates, Byron D.
    Branda, Neil R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (44) : 15766 - 15772
  • [6] Remote-Control Photoswitching Using NIR Light
    Carling, Carl-Johan
    Boyer, John-Christopher
    Branda, Neil R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) : 10838 - +
  • [7] Chen Y., 2023, Adv. Funct. Mater, V33
  • [8] Ring-opening and -closure reaction dynamics of a photochromic dithienylethene derivative
    Ern, J
    Bens, AT
    Martin, HD
    Kuldova, K
    Trommsdorff, HP
    Kryschi, C
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (09) : 1654 - 1660
  • [9] Switching Diarylethenes Reliably in Both Directions with Visible Light
    Fredrich, Sebastian
    Goestl, Robert
    Herder, Martin
    Grubert, Lutz
    Hecht, Stefan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (03) : 1208 - 1212
  • [10] Frisch G. W. T. M. J., 2009, GAUSSIAN 09, P02