One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

被引:734
作者
Gingras, Marc [1 ,2 ]
机构
[1] CNRS, UMR 7325, F-13288 Marseille, France
[2] Aix Marseille Univ, CINaM, F-13288 Marseille, France
关键词
NONLINEAR-OPTICAL PROPERTIES; CHARGE-TRANSFER COMPLEXATION; DETECTED CIRCULAR-DICHROISM; PHOTO-ASYMMETRIC SYNTHESIS; LANGMUIR-BLODGETT-FILMS; CHIRAL RECOGNITION; MOLECULAR CHIRALITY; ELECTROCHIROPTICAL RESPONSE; CHIROPTICAL PROPERTIES; NATIVE CYCLODEXTRINS;
D O I
10.1039/c2cs35134j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbohelicenes are a class of fascinating chiral helical molecules which have a rich history in chemistry. Over a period of almost 100 years, chemists have developed many methods to prepare them in a racemic or in a non-racemic form. They also possess a series of interesting chiral, physical, electronic and optical properties. However, their utilization in chemistry or chemistry-related fields has rarely appeared in a detailed and comprehensive review. It is the purpose of this review to collect fundamental applications and functions involving carbohelicenes in various disciplines such as in materials science, in nanoscience, in biological chemistry and in supramolecular chemistry. From the numerous synthetic methodologies reported up to now, carbohelicenes and their derivatives can be tailor-made for a better involvement in several subfields. Among those domains are: nanosciences, chemosensing, liquid crystals, molecular switches, polymers, foldamers, supramolecular materials, molecular recognition, conductive and opto-electronic materials, nonlinear optics, chirality studies and asymmetric synthesis. Helicene chemistry is now at a developmental stage, where sufficient application data are now collected and are extremely useful. They provide many more ideas for setting up the basis for future innovative applications.
引用
收藏
页码:1051 / 1095
页数:45
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共 250 条
[111]   Toward intelligent molecular machines: Directed motions of biological and artificial molecules and assemblies [J].
Kinbara, K ;
Aida, T .
CHEMICAL REVIEWS, 2005, 105 (04) :1377-1400
[112]   Optically active phthalocyanines [J].
Kobayashi, N .
COORDINATION CHEMISTRY REVIEWS, 2001, 219 :99-123
[113]   Artificial molecular rotors [J].
Kottas, GS ;
Clarke, LI ;
Horinek, D ;
Michl, J .
CHEMICAL REVIEWS, 2005, 105 (04) :1281-1376
[114]   Light-driven monodirectional molecular rotor [J].
Koumura N. ;
Zijistra R.W.J. ;
Van Delden R.A. ;
Harada N. ;
Feringa B.L. .
Nature, 1999, 401 (6749) :152-155
[115]   Methyl group-induced helicity in 1,4-dimethylbenzo[c]phenanthrene and its metabolites:: Synthesis, physical, and biological properties [J].
Lakshman, MK ;
Kole, PL ;
Chaturvedi, S ;
Saugier, JH ;
Yeh, HJC ;
Glusker, JP ;
Carrell, HL ;
Katz, AK ;
Afshar, CE ;
Dashwood, WM ;
Kenniston, G ;
Baird, WM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12629-12636
[116]   Discotic liquid crystals:: From tailor-made synthesis to plastic electronics [J].
Laschat, Sabine ;
Baro, Angelika ;
Steinke, Nelli ;
Giesselmann, Frank ;
Haegele, Constanze ;
Scalia, Giusy ;
Judele, Roxana ;
Kapatsina, Elisabeth ;
Sauer, Sven ;
Schreivogel, Alina ;
Tosoni, Martin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (26) :4832-4887
[117]   Synthetic methodology towards novel polyphenylated naphthalocyanines [J].
Lee, Chi-Hang ;
Sooksimuang, Thanasat ;
Mandal, Braja K. .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2006, 10 (03) :135-139
[118]   Dynamic chirality:: Molecular shuttles and motors [J].
Leigh, David A. ;
Perez, Emilio M. .
SUPRAMOLECULAR CHIRALITY, 2006, 265 :185-208
[119]   Photo-asymmetric synthesis of helicenes in liquid crystals [J].
Lin, YH ;
Chien, LC .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1997, 301 :267-282
[120]   Extended surface chirality from supramolecular assemblies of adsorbed chiral molecules [J].
Lorenzo, MO ;
Baddeley, CJ ;
Muryn, C ;
Raval, R .
NATURE, 2000, 404 (6776) :376-379