Dinaphthoporphycenes: Synthesis and Nonlinear Optical Studies

被引：104

作者：

Sarma, Tridib ^{[1
]}

Panda, Pradeepta K. ^{[1
,2
]}

Anusha, P. T. ^{[2
]}

Rao, S. Venugopal ^{[2
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

[2] Univ Hyderabad, ACRHEM, Hyderabad 500046, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 02期

关键词：

2-PHOTON ABSORPTION; 3-PHOTON ABSORPTION; PORPHYCENE; PORPHYRINS; PYRROLOINDOLES; COMPLEXES; MOLECULES; HYDROGEN;

D O I：

10.1021/ol102378g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naphthobipyrrole-derived porphycenes are synthesized for the first time via McMurry coupling of the beta-alkylated 2,9-diformylnaphthobipyrrole derivatives, which in turn were prepared easily from 2,3-naphthalene bishydrazine in four steps. Insertion of nickel into the porphycene core results in transformation of the rectangular N4-core into a square type geometry owing to the fusion of naphthalene moiety onto the bipyrrole entities. These porphycenes show large, intensity dependent three-photon absorption.

引用

页码：188 / 191

页数：4

共 44 条

[1] 9,10,19,20-Tetraarylporphycenes [J].

Anju, K. S. ;

Ramakrishnan, S. ;

Thomas, Ajesh P. ;

Suresh, Eringathodi ;

Srinivasan, Alagar .

ORGANIC LETTERS, 2008, 10 (24) :5545-5548

[2] Diethyl 2,7-dibromo-4H,5H-thieno[3,2-b:4,5-b′]dipyrrole-3,6-dicarboxylate:: A key intermediate for a diversity oriented synthesis of 2,7,12,17-tetraarylporphycenes [J].

Arad, O ;

Morros, J ;

Batllori, X ;

Teixidó, J ;

Nonell, S ;

Borrell, JI .

ORGANIC LETTERS, 2006, 8 (05) :847-850

[3] Two-photon absorption in tetraphenylporphycenes:: Are porphycenes better candidates than porphyrins for providing optimal optical properties for two-photon photodynamic therapy? [J].

Arnbjerg, Jacob ;

Jimenez-Banzo, Ana ;

Paterson, Martin J. ;

Nonell, Santi ;

Borrell, Jose I. ;

Christiansen, Ove ;

Ogilby, Peter R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5188-5199

[4] Metalloporphycenes: Synthesis and Characterization of (Pentamethylcyclopentadienyl)ruthenium Sitting-Atop and π-Complexes [J].

Cuesta, Luciano ;

Karnas, Elizabeth ;

Lynch, Vincent M. ;

Chen, Ping ;

Shen, Jing ;

Kadish, Karl M. ;

Ohkubo, Kei ;

Fukuzumi, Shunichi ;

Sessler, Jonathan L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (37) :13538-13547

[5] Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds [J].

de la Torre, G ;

Váquez, P ;

Agulló-López, F ;

Torres, T .

CHEMICAL REVIEWS, 2004, 104 (09) :3723-3750

[6] Energy relaxation paths in matrix-isolated excited molecules: Comparison of porphycene with dibenzoporphycenes [J].

Dobkowski, J ;

Lobko, Y ;

Gawinkowski, S ;

Waluk, J .

CHEMICAL PHYSICS LETTERS, 2005, 416 (1-3) :128-132

[7] Spectroscopy and photophysics of tetraalkyldibenzoporphycenes [J].

Dobkowski, J ;

Galievsky, V ;

Starukhin, A ;

Vogel, E ;

Waluk, J .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (26) :4966-4971

[8] Extremely strong near-IR two-photon absorption in conjugated porphyrin dimers: Quantitative description with three-essential-states model [J].

Drobizhev, M ;

Stepanenko, Y ;

Dzenis, Y ;

Karotki, A ;

Rebane, A ;

Taylor, PN ;

Anderson, HL .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (15) :7223-7236

[9] Uncovering coherent domain structure in a series of π-conjugated dendrimers by simultaneous three-photon absorption [J].

Drobizhev, M ;

Karotki, A ;

Kruk, M ;

Dzenis, Y ;

Rebane, A ;

Suo, Z ;

Spangler, CW .

JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (14) :4221-4226

[10] Stepwise elongation effect on the two-photon absorption of self-assembled butadiyne porphyrins [J].

Dy, Joanne ;

Ogawa, Kazuya ;

Kamada, Kenji ;

Ohta, Koji ;

Kobuke, Yoshiaki .

CHEMICAL COMMUNICATIONS, 2008, (29) :3411-3413

← 1 2 3 4 5 →