Cyclic 2,12-Porphyrinylene Nanorings as a Porphyrin Analogue of Cycloparaphenylenes

被引：81

作者：

Jiang, Hua-Wei ^{[1
]}

Tanaka, Takayuki ^{[1
]}

Mori, Hirotaka ^{[1
]}

Park, Kyu Hyung ^{[2
,3
]}

Kim, Dongho ^{[2
,3
]}

Osuka, Atsuhiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

[2] Yonsei Univ, Spect Lab Funct Elect Syst, Seoul 120749, South Korea

[3] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

BOTTOM-UP SYNTHESIS; TEMPLATE-DIRECTED SYNTHESIS; ENERGY-TRANSFER; CARBON; ARRAYS; STEP;

D O I：

10.1021/ja513102m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

beta-to-beta Directly linked cyclic Ni(II) porphyrin trimer, tetramer, and pentamer ([3]CP, [4]CP, and [5]CP) have been synthesized by reaction of a 2,12-diborylated Ni(II) porphyrin with Pt(cod)Cl-2 followed by reductive elimination. The structures of these cyclic porphyrin arrays have been revealed by X-ray diffraction analysis. The strain energies of these cyclic oligomers are calculated to be 77, 57, and 47 kcal/mol for [3]CP, [4]CP, and [5]CP, respectively. Intramolecular excitation energy hopping was observed between the (3)(d,d) states of the Ni(II) porphyrins with rates of 3.0, 4.4, and 4.6 ps for [3]CP, [4]CP, and [5]CP, respectively, reflecting the close proximity of the Ni(II) centers.

引用

页码：2219 / 2222

页数：4

共 45 条

[1] AMINE-TEMPLATE-DIRECTED SYNTHESIS OF CYCLIC PORPHYRIN OLIGOMERS [J].

ANDERSON, HL ;

SANDERS, JKM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1400-1403

[2] EXPANDING ROLES FOR TEMPLATES IN SYNTHESIS [J].

ANDERSON, S ;

ANDERSON, HL ;

SANDERS, JKM .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :469-475

[3]

[Anonymous], 2012, ANGEW CHEM INT ED

[4]

Aratani N., 2009, ACCOUNTS CHEM RES, V42, P1922

[5] A meso-meso directly linked octameric porphyrin square [J].

Aratani, Naoki ;

Osuka, Atsuhiro .

CHEMICAL COMMUNICATIONS, 2008, (34) :4067-4069

[6] DFT Study of Cycloparaphenylenes and Heteroatom-Substituted Nanohoops [J].

Bachrach, Steven M. ;

Stueck, David .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6595-6604

[7] Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes [J].

Eisenberg, David ;

Shenhar, Roy ;

Rabinovitz, Mordecai .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (08) :2879-2890

[8]

Evans PJ, 2014, NAT CHEM, V6, P404, DOI [10.1038/NCHEM.1888, 10.1038/nchem.1888]

[9] ALTERNATIVE APPROACH TO PROBLEM OF ASSESSING DESTABILIZATION ENERGIES (STRAIN ENERGIES) IN CYCLIC HYDROCARBONS [J].

GEORGE, P ;

TRACHTMAN, M ;

BOCK, CW ;

BRETT, AM .

TETRAHEDRON, 1976, 32 (03) :317-323

[10] THE STRUCTURE-DIRECTED SYNTHESIS OF CYCLACENE AND POLYACENE DERIVATIVES [J].

GIRRESER, U ;

GIUFFRIDA, D ;

KOHNKE, FH ;

MATHIAS, JP ;

PHILP, D ;

STODDART, JF .

PURE AND APPLIED CHEMISTRY, 1993, 65 (01) :119-125

← 1 2 3 4 5 →