Coordination-Driven Self-Assembly of 2D-Metallamacrocycles Using a New Carbazole-Based Dipyridyl Donor: Synthesis, Characterization, and C-60 Binding Study

Shanmugaraju, Sankarasekaran and Vajpayee, Vaishali and Lee, Sunmi and Chi, Ki-Whan and Stang, Peter J and Mukherjee, Partha Sarathi (2012) Coordination-Driven Self-Assembly of 2D-Metallamacrocycles Using a New Carbazole-Based Dipyridyl Donor: Synthesis, Characterization, and C-60 Binding Study. In: Inorganic Chemistry, 51 (8). pp. 4817-4823.

	PDF ic300199j.pdf - Published Version Restricted to Registered users only Download (2360Kb) | Request a copy
	PDF ic300199j_si_001.pdf - Supplemental Material Restricted to Registered users only Download (1552Kb) | Request a copy
	Plain Text ic2020989_si_002.cif - Supplemental Material Restricted to Registered users only Download (24Kb) | Request a copy

Abstract

A new carbazole-based 90 degrees dipyridyl donor 3,6-di(4-pyridylethynyl)carbazole (L) containing carbazole-ethynyl functionality is synthesized in reasonable yield using the Sonagashira coupling reaction. Multinuclear NMR, electrospray ionization-mass spectrometry (ESI-MS), including single crystal X-ray diffraction analysis characterized this 90 degrees building unit. The stoichiometry combination of L with several Pd(II)/Pt(II)-based 90 degrees acceptors (1a-1d) yielded 2 + 2] self-assembled metallacycles (2a-2d) under mild conditions in quantitative yields 1a = cis-(dppf)Pd(OTf)(2); 1b = cis-(dppf)Pt(OTf)(2); 1c = cis-(tmen)Pd(NO3)(2); 1d = 3,6-bis{trans-Pt(C C) (PEt3)(2)(NO3))carbazole]. All these macrocycles were characterized by various spectroscopic techniques, and the molecular structure of 2a was unambiguously determined by single crystal X-ray diffraction analysis. Incorporation of ethynyl functionality to the carbazole backbone causes the resulted macrocycles (2a-2d) to be pi-electron rich and thereby exhibit strong emission characteristics. The macrocycle 2a has a large internal concave aromatic surface. The fluorescence quenching study suggests that 2a forms a similar to 1:1 complex with C-60 with a high association constant of K-sv = 1.0 X 10(5) M-1.

Item Type:	Journal Article
Additional Information:	Copyright of this article is belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	22 Aug 2012 04:57
Last Modified:	22 Aug 2012 04:58
URI:	http://eprints.iisc.ernet.in/id/eprint/44459

Actions (login required)

View Item