NDLI: Synthesis and versatile supramolecular self-assembly of the 5,15-bis(4-hydroxyphenyl)-10,20-bis(4-carboxyphenyl)porphyrin scaffold

Content Provider	Royal Society of Chemistry (RSC)
Author	Vinodu, Mikki Goldberg, Israel
Copyright Year	2004
Abstract	This study reports the synthesis of the 5,15-bis(4-hydroxyphenyl)-10,20-bis(4-carboxyphenyl)porphyrin (BBP) moiety, and its versatile self-assembly into multiporphyrin hydrogen-bonding ‘polymers’ in four different reaction and crystallization conditions. In two cases the polymers are sustained by characteristic intermolecular cyclic dimeric (COOH)2 hydrogen-bond synthons between the carboxyphenyl functions of neighboring species, which face one another along a common equatorial axis of the porphyrin building blocks. The hydroxyphenyl substituents, which are directed perpendicular to the porphyrin chains, form either O–H⋯O(dioxane) or O–H⋯N(pyridine) weak hydrogen bonds by donating their protons to the solvent guest species. In the third example, the multiporphyrin chains are tessellated by rather unusual pairs of OH⋯OC(OH) hydroxyl–carboxyl hydrogen bonds between cis-related arms of adjacent porphyrin species along opposite directions of the polymer. Here the carboxylic protons are donated to the carbonyl site of the ethyl benzoate guest, thus linking the latter to the side surfaces of the polymeric chain. The fourth structure, which involves chain polymers of deprotonated porphyrin building blocks, is sustained by strong symmetric [–COO⋯H⋯OOC–]− hydrogen bonds along the chains. These chains aggregate further into complex three-dimensional architecture by weaker hydrogen bonds through bridging water molecules. The observed diversity of the intermolecular binding patters suggests that the BBP scaffold is not well suited for a programmed construction of network solids.
Starting Page	215
Ending Page	220
Page Count	6
File Format	HTM / HTML PDF
ISSN	14668033
Volume Number	6
Issue Number	37
Journal	CrystEngComm
DOI	10.1039/b407157c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Polymer Chief operating officer Open-pit mining Network covalent bonding BBP Pyridine Porphyrin Ethyl benzoate Carbonyl group Molecular self-assembly Solvent Synthon 1,4-Dioxane Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Materials Science

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

5,15-Bis(3,5-di-tert-butylphenyl)-10,20-bis(phenylethynyl)porphyrin

Bis{μ-ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}bis[aqua(4-{[4-(ethoxycarbonyl)phenyl]diazenyl}phenolato-κO){ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}potassium]

Toxicity Prediction of meso-5,15-di(3,4-bis(carboxymethylenoxy)phenyl) porphyrin and meso-5,15-di(3,4-bis(carboxymethylenoxy)phenyl),10,20- diphenyl porphyrin

Supramolecular self-assembly of porphyrinic materials by design. Non-centrosymmetric architectures of the 5-(3′-pyridyl)-10,15,20-tris(4′-carboxyphenyl) and 5-(2′-quinolyl)-10,15,20-tris(4′-hydroxyphenyl) porphyrins

Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold

Porphyrin networks. Synthesis and supramolecular self-assembly of 5,10,15-tri(4-hydroxyphenyl)-20-(2-quinolyl) metalloporphyrins

Novel btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] systems: a versatile motif for the formation of supramolecular self-assembly structures

5,15-Bis(3,5-di-tert-butyl-phen-yl)-10,20-bis-(phenyl-ethyn-yl)porphyrin.

5,15-Bis(3,5-di-tert-butylphenyl)-10,20-bis(phenylethynyl)porphyrin

Synthesis and versatile supramolecular self-assembly of the 5,15-bis(4-hydroxyphenyl)-10,20-bis(4-carboxyphenyl)porphyrin scaffold

Similar Documents

5,15-Bis(3,5-di-tert-butylphenyl)-10,20-bis(phenylethynyl)porphyrin

Bis{μ-ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}bis[aqua(4-{[4-(ethoxycarbonyl)phenyl]diazenyl}phenolato-κO){ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}potassium]

Toxicity Prediction of meso-5,15-di(3,4-bis(carboxymethylenoxy)phenyl) porphyrin and meso-5,15-di(3,4-bis(carboxymethylenoxy)phenyl),10,20- diphenyl porphyrin

Supramolecular self-assembly of porphyrinic materials by design. Non-centrosymmetric architectures of the 5-(3′-pyridyl)-10,15,20-tris(4′-carboxyphenyl) and 5-(2′-quinolyl)-10,15,20-tris(4′-hydroxyphenyl) porphyrins

Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold

Porphyrin networks. Synthesis and supramolecular self-assembly of 5,10,15-tri(4-hydroxyphenyl)-20-(2-quinolyl) metalloporphyrins

Novel btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] systems: a versatile motif for the formation of supramolecular self-assembly structures

5,15-Bis(3,5-di-tert-butyl-phen-yl)-10,20-bis-(phenyl-ethyn-yl)porphyrin.

5,15-Bis(3,5-di-tert-butyl­phen­yl)-10,20-bis­(phenyl­ethyn­yl)porphyrin

Synthesis and versatile supramolecular self-assembly of the 5,15-bis(4-hydroxyphenyl)-10,20-bis(4-carboxyphenyl)porphyrin scaffold

5,15-Bis(3,5-di-tert-butylphenyl)-10,20-bis(phenylethynyl)porphyrin