Synthesis and Nondestructive Information Processing Properties of Diarylethene-Based Porphyrin Derivative

doi:10.11944/j.issn.1000-0518.2017.05.160313

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (5): 527-533.DOI: 10.11944/j.issn.1000-0518.2017.05.160313

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Synthesis and Nondestructive Information Processing Properties of Diarylethene-Based Porphyrin Derivative

LIU Cheng,HU Bingcheng(),YU Chuanming,LI Jiting

School of Chemical Engeering,Nanjing University of Science and Technology,Nanjing 210094,China

Received:2016-08-09 Accepted:2016-11-28 Published:2017-05-02 Online:2017-05-02
Contact: HU Bingcheng

Abstract

Abstract:

The dithienylethene compounds offer broad application prospects in optical memory media due to their great performance in reversible chemical transition with irradiation of appropriate light. In this paper, a novel 1-(2-methyl-3-thienyl)-2-{2-methyl-5-{4-[4-(10,15,20-triphenyl-5-porphinyl)phenyl]aminocarbonylphenyl}-3-thienyl}cyclopentene(DTE-TPP) was synthesized using 2-methylthiophene, benzaldehyde and pyrrole as starting materials, and its structure was fully characterized by nuclear magnetic resonance spectroscopy(NMR), mass spectrometry(MS) and Fourier transform infrared spectrometer(FTIR). Photochromic properties of the target compound, fatigue resistance and nondestructive readout capability were investigated by UV-Vis spectra and fluorescent emission spectroscopy. The UV-Vis spectra results indicate that DTE-TPP undergoes bistable and reversible photochromic reactions under irradiation, which is repeated at least eight times, at 254 and 660 nm light. The ring-opened form and ring-closed form of DTE-TPP exhibit great contrasts in fluorescence spectra(λ_ex=520 nm) and a nondestructive readout method may be achived.

Key words: porphyrin, dithienylethene, photochromic, nondestructive readout

LIU Cheng,HU Bingcheng,YU Chuanming,LI Jiting. Synthesis and Nondestructive Information Processing Properties of Diarylethene-Based Porphyrin Derivative[J]. Chinese Journal of Applied Chemistry, 2017, 34(5): 527-533.

References

[1]	Irie M,Fukaminato T,Sasaki T,et al. Organic Chemistry:A Digital Fluorescent Molecular Photoswitch[J]. Nature,2002,420(6917):759-760.
[2]	Chan J C H,Lam W H,Yam V W W. A Highly Efficient Silole-Containing Dithienylethene with Excellent Ehermal Stability and Fatigue Resistance:A Promising Candidate for Optical Memory Storage Materials[J]. J Am Chem Soc,2014,136(49):16994-16997.
[3]	Zou Y,Yi T,Xiao S,et al. Amphiphilic Diarylethene as a Photoswitchable Probe for Imaging Living Cells[J]. J Am Chem Soc,2008,130(47):15750-15751.
[4]	GONG Tao,FENG Jiachun,WEI Wei,et al. Recent Progress in Diarylethene as a Photoswitching Unit[J]. Prog Chem,2006,18(6):698-706 (in Chinese). 龚涛,冯嘉春,韦伟,等. 二芳基乙烯类化合物用作光开关的最新进展[J]. 化学进展,2006,18(6):698-706.
[5]	Areephong J,Logtenberg H,Browne W R,et al. Symmetric Six-Fold Arrays of Photo- and Electrochromic Dithienylethene Switches[J]. Org Lett,2010,12(9):2132-2135.
[6]	Irie M,Yamaguchi T,Nakazumi H,et al. Radiation-Induced Coloration of Photochromic Dithienylethene Derivatives[J]. Bull Chem Soc Jpn,1999,72(5):1139-1142.
[7]	Osuka A,Daisuke F,Shinmori H,et al. Synthesis and Photoisomerization of Dithienylethene-Bridged Diporphyrin[J]. J Org Chem,2001,66(11):3913-3923.
[8]	Uno K,Niikura H,Morimoto M,et al. In Situ Preparation of Highly Fluorescent Dyes upon Photoirradiation[J]. J Am Chem Soc,2011,133(34):13558-13564.
[9]	Irie M,Fukaminato T,Matsuda K,et al. Photochromism of Diarylethene Molecules and Crystals:Memories, Switches, and Actuators[J]. Chem Rev,2014,114(24):12174-12277.
[10]	Jiang J Y,Wang S,Yuan W F,et al. Highly Fluorescent Contrast for Rewritable Optical Storage Based on Photochromic Bisthienylethene-Bridged Naphthalimide Dimer[J]. Chem Mater,2006,18(2):235-237.
[11]	Norsten T B,Branda N R. Photoregulation of Fluorescence in a Porphyrinic Dithienylethene Photochrome[J]. J Am Chem Soc,2001,123(8):1784-1785.
[12]	Zhang J B,Li C P,Huo T R,et al. Photochemical Reaction of Magnesium Tetraphenylporphyrin with Sulfur Dioxide[J]. Chinese Chem Lett,2010,21(7):787-789.
[13]	Seol M L,Choi S J,Choi J M,et al. Hybrid Porphyrin-Silicon Nanowire Field-Effect Transistor by Opto-Electrical Excitation[J]. ACS Nano,2012,6(9):7885-7892.
[14]	ZHENG Chunmei,WANG Tingting,ZENG Heping,et al. Synthesis and Photochromic Properties of Diarylethene-Based Porphyrin Derivatives and Its Metal Complexes[J]. Chinese J Org Chem,2012,32(4):719-726 (in Chinese). 郑春梅,王婷婷,曾和平,等. 卟啉-二芳基乙烯分子及其金属配合物的合成与光致变色特性[J]. 有机化学,2012,32(4):719-726.
[15]	Kim H J,Jang J H,Choi H,et al. Photoregulated Fluorescence Switching in Axially Coordinated Tin(Ⅳ) Porphyrinic Dithienylethene[J]. Inorg Chem,2008,47(7):2411-2415.
[16]	Straight S D,Andreasson J,Kodis G,et al. Molecular AND and INHIBIT Gates Based on Control of Porphyrin Fluorescence by Photochromes[J]. J Am Chem Soc,2005,127(26):9403-9409.
[17]	Tyler B N,Neil R B. Axially Coordinated Porphyrinic Photechromes for Non-destructive Information Processing[J]. Adv Mater,2001,13(5):347-349.
[18]	Gaware V S,Haakerud M,Monika L K,et al. Tetraphenylporphyrin Tethered Chitosan Based Carriers for Photochemical Transfection[J]. J Med Chem,2013,56(3):807-819.
[19]	Linda N L,Jaap J D,Jan H E,et al. Syntheses of Dithienylcyclopentene Optical Molecular Switches[J]. Eur J Org Chem,2003,(1):155-166.
[20]	Kobatake S,Uchida K,Tsuchida E,et al. Photochromism of Diarylethenes Having Isopropyl Groups at the Reactive Carbons. Thermal Cycloreversion of the Closed-Ring Isomers[J]. Chem Lett,2000,(11):1340-1341.
[21]	XU Haijun,WANG Xiaoge. Advances on Application of Diarylethene Photochromic Derivatives[J]. Chem Reag,2012,34(6):513-518 (in Chinese). 徐海军,王晓格. 二芳基乙烯类光致变色单元应用研究进展[J]. 化学试剂,2012,34(6):513-518.
[22]	Nakagawa T,Hasegawa Y,Kawai T. Nondestructive Luminescence Intensity Readout of a Photochromic Lanthanide(Ⅲ) Complex[J]. Chem Commun,2009,(32):5630-5632.

Synthesis and Nondestructive Information Processing Properties of Diarylethene-Based Porphyrin Derivative

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