Recent Advances in Applications of Fluorescent Perylenediimide and Perylenemonoimide Dyes in Bioimaging, Photothermal and Photodynamic Therapy

被引:33
作者
Krupka, Oksana [1 ]
Hudhomme, Pietrick [2 ]
机构
[1] Univ Angers, Inserm, CNRS, MINT,SFR ICAT, F-49000 Angers, France
[2] Univ Angers, CNRS, MOLTECH Anjou, SFR MATRIX, F-49000 Angers, France
关键词
perylenediimide; perylenemonoimide; dyes; fluorescence; bioimaging; photothermal therapy; photodynamic therapy; cancer therapy; theranostics; EFFICIENT PHOTOACOUSTIC AGENTS; NON-FULLERENE ACCEPTORS; SOLAR-CELLS; DIIMIDES SYNTHESIS; BISIMIDE DYES; WATER; NANOPARTICLES; DERIVATIVES; STATE; DESIGN;
D O I
10.3390/ijms24076308
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The emblematic perylenediimide (PDI) motif which was initially used as a simple dye has undergone incredible development in recent decades. The increasing power of synthetic organic chemistry has allowed it to decorate PDIs to achieve highly functional dyes. As these PDI derivatives combine thermal, chemical and photostability, with an additional high absorption coefficient and near-unity fluorescence quantum yield, they have been widely studied for applications in materials science, particularly in photovoltaics. Although PDIs have always been in the spotlight, their asymmetric counterparts, perylenemonoimide (PMI) analogues, are now experiencing a resurgence of interest with new efforts to create architectures with equally exciting properties. Namely, their exceptional fluorescence properties have recently been used to develop novel systems for applications in bioimaging, biosensing and photodynamic therapy. This review covers the state of the art in the synthesis, photophysical characterizations and recently reported applications demonstrating the versatility of these two sister PDI and PMI compounds. The objective is to show that after well-known applications in materials science, the emerging trends in the use of PDI- and PMI-based derivatives concern very specific biomedicinal applications including drug delivery, diagnostics and theranostics.
引用
收藏
页数:51
相关论文
共 157 条
[91]   Highly biocompatible amphiphilic perylenediimide derivative for bioimaging [J].
Park, Jin-Kyung ;
Kim, Ran Hee ;
Prabhakaran, Prem ;
Kim, Sehoon ;
Lee, Kwang-Sup .
OPTICAL MATERIALS EXPRESS, 2016, 6 (05) :1420-1428
[92]   Synthesis, Electrochemical and Optical Absorption Properties of New Perylene-3,4:9,10-bis(dicarboximide) and Perylene-3,4:9,10-bis(benzimidazole) Derivatives [J].
Perrin, Lara ;
Hudhomme, Pietrick .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) :5427-5440
[93]   Ligand-Localized Triplet-State Photophysics in a Platinum(II) Terpyridyl Perylenediimideacetylide [J].
Prusakova, Valentina ;
McCusker, Catherine E. ;
Castellano, Felix N. .
INORGANIC CHEMISTRY, 2012, 51 (15) :8589-8598
[94]   Aromatic imide/amide-based organic small-molecule emitters for organic light-emitting diodes [J].
Qin, Yuanyuan ;
Li, Guoping ;
Qi, Ting ;
Huang, Hui .
MATERIALS CHEMISTRY FRONTIERS, 2020, 4 (06) :1554-1568
[95]   QUATERRYLENEBIS(DICARBOXIMIDES) [J].
QUANTE, H ;
MULLEN, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (12) :1323-1325
[96]   Recent progress in the development of n-type organic semiconductors for organic field effect transistors [J].
Quinn, Jesse T. E. ;
Zhu, Jiaxin ;
Li, Xu ;
Wang, Jinliang ;
Li, Yuning .
JOURNAL OF MATERIALS CHEMISTRY C, 2017, 5 (34) :8654-8681
[97]   SOLUBLE PERYLENE FLUORESCENT DYES WITH HIGH PHOTOSTABILITY [J].
RADEMACHER, A ;
MARKLE, S ;
LANGHALS, H .
CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (08) :2927-2934
[98]   Selective bromination of perylene diimides under mild conditions [J].
Rajasingh, Paramasivan ;
Cohen, Revital ;
Shirman, Elijah ;
Shimon, Linda J. W. ;
Rybtchinski, Boris .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :5973-5979
[99]   Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials [J].
Rocard, Lou ;
Goujon, Antoine ;
Hudhomme, Pietrick .
MOLECULES, 2020, 25 (06)
[100]   Original Suzuki-Miyaura Coupling Using Nitro Derivatives for the Synthesis of Perylenediimide-Based Multimers [J].
Rocard, Lou ;
Hatych, Danylo ;
Chartier, Thomas ;
Cauchy, Thomas ;
Hudhomme, Pietrick .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (47) :7635-7643