Supramolecular Chirality in Porphyrin Self-Assembly Systems in Aqueous Solution

被引:3
作者
Travagliante, Gabriele [1 ]
Gaeta, Massimiliano [1 ]
Purrello, Roberto [1 ]
D'Urso, Alessandro [1 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
Porphyrins; self-assembly; supramolecular chirality; chiral induction; circular dichroism; UV/Vis spectroscopy; HELICITY INDUCTION; J-AGGREGATE; HYDRODYNAMIC-FORCES; CIRCULAR-DICHROISM; KINETIC CONTROL; AMPLIFICATION; POLY(PHENYLACETYLENE); MEMORY; ACID; BEARING;
D O I
10.2174/1385272826666220330112648
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The self-assembly process appears as a powerful and attractive strategy for constructing complex supramolecules by the spontaneous organization of appropriate building blocks. In this scenario, water-soluble porphyrinoids lend themselves as ideal paradigms to disclose the self-assembly phenomenon by exploiting their well-known tendency to build aggregates in aqueous media via weak non-covalent forces. Nevertheless, the spontaneous organization of achiral porphyrins can result in a final chiral superstructure moving away from single-molecule behaviour to supramolecular chirality. Therefore, over the years numerous attempts have been implemented to investigate how a porphyrin aggregate, made up of achiral monomers, becomes not-symmetric and which processes govern the bias for a certain enantiomeric assembly rather than another. Thus, in this mini-review, we exclusively discuss the main strategies for designing and building chiral aggregates in water from achiral porphyrin monomers, with particular regard to their chiroptical features.
引用
收藏
页码:563 / 579
页数:17
相关论文
共 124 条
[1]   Probing the determinants of porosity in protein frameworks: co-crystals of cytochrome c and an octa-anionic calix[4]arene [J].
Alex, Jimi M. ;
Brancatelli, Giovanna ;
Volpi, Stefano ;
Bonaccorso, Carmela ;
Casnati, Alessandro ;
Geremia, Silvan ;
Crowley, Peter B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (02) :211-214
[2]   Supramolecular chiral functional materials [J].
Amabilino, David B. ;
Veciana, Jaurne .
SUPRAMOLECULAR CHIRALITY, 2006, 265 :253-302
[3]   Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels-Alder adducts [J].
Arlegui, Aitor ;
Soler, Bernat ;
Galindo, Alex ;
Arteaga, Oriol ;
Canillas, Adolf ;
Ribo, Josep M. ;
El-Hachemi, Zoubir ;
Crusats, Joaquim ;
Moyano, Albert .
CHEMICAL COMMUNICATIONS, 2019, 55 (81) :12219-12222
[4]   Reversible and irreversible emergence of chiroptical signals in J-aggregates of achiral 4-sulfonatophenyl substituted porphyrins: intrinsic chirality vs. chiral ordering in the solution [J].
Arteaga, Oriol ;
El-Hachemi, Zoubir ;
Canillas, Adolf ;
Crusats, Joaquim ;
Rovira, Meritxell ;
Ribo, Josep M. .
CHEMICAL COMMUNICATIONS, 2016, 52 (72) :10874-10877
[5]   Emergence of Supramolecular Chirality by Flows [J].
Arteaga, Oriol ;
Canillas, Adolf ;
Crusats, Joaquim ;
El-Hachemi, Zoubir ;
Llorens, Joan ;
Sacristan, Eduardo ;
Ribo, Josep M. .
CHEMPHYSCHEM, 2010, 11 (16) :3511-3516
[6]   Helical structural change in poly((4-carboxyphenyl)acetylene) by acid-base complexation with an optically active amine [J].
Ashida, Y ;
Sato, T ;
Morino, K ;
Maeda, K ;
Okamoto, Y ;
Yashima, E .
MACROMOLECULES, 2003, 36 (09) :3345-3350
[7]   Chlorins programmed for self-assembly [J].
Balaban, TS ;
Tamiaki, H ;
Holzwarth, AR .
SUPERMOLECULAR DYE CHEMISTRY, 2005, 258 :1-38
[8]   Template-imprinted chiral porphyrin aggregates [J].
Bellacchio, E ;
Lauceri, R ;
Gurrieri, S ;
Scolaro, LM ;
Romeo, A ;
Purrello, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12353-12354
[9]   Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].
Berova, Nina ;
Di Bari, Lorenzo ;
Pescitelli, Gennaro .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931
[10]   Factors driving the self-assembly of water-soluble calix[4]arene and gemini guests: a combined solution, computational and solid-state study [J].
Bonaccorso, Carmela ;
Brancatelli, Giovanna ;
Forte, Giuseppe ;
Arena, Giuseppe ;
Geremia, Silvano ;
Sciotto, Domenico ;
Sgarlata, Carmelo .
RSC ADVANCES, 2014, 4 (96) :53575-53587