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Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.

ABSTRACT: Two aldehydes, 2,6-diacetamido-4-formylpyridine (7) and 1-butyl-6-formyluracil (11), are used to synthesize five pyridyl and four uracyl meso-subsituted porphyrins. With these complementary porphyrin building blocks, it is possible to build various types of multi-porphyrin supramolecules with different spatial relationships in predefined geometries. The formation and properties of self-complementary dimers and a closed tetrameric square are presented as a basis of comparison to the latter system in the solid state. An X-ray structure of 5,10-bis(4-tert-butylphenyl)-15,20-bis(3,5-diacetamido-4-pyridyl)porphyrin confirms its molecular structure and reveals a hydrogen-bonded supramolecular organization mediated by water molecules.

SUBMITTER: Shi X

PROVIDER: S-EPMC6207087 | biostudies-literature | 2001 Oct

REPOSITORIES: biostudies-literature

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Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.

Shi X X Barkigia K M KM Fajer J J Drain C M CM

The Journal of organic chemistry 20011001 20

Two aldehydes, 2,6-diacetamido-4-formylpyridine (7) and 1-butyl-6-formyluracil (11), are used to synthesize five pyridyl and four uracyl meso-subsituted porphyrins. With these complementary porphyrin building blocks, it is possible to build various types of multi-porphyrin supramolecules with different spatial relationships in predefined geometries. The formation and properties of self-complementary dimers and a closed tetrameric square are presented as a basis of comparison to the latter system ...[more]

PMID: 11578199

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Project description:Single-walled carbon nanotubes (SWNTs) have been used extensively for sensor fabrication due to its high surface to volume ratio, nanosized structure and interesting electronic property. Lack of selectivity is a major limitation for SWNTs-based sensors. However, surface modification of SWNTs with a suitable molecular recognition system can enhance the sensitivity. On the other hand, porphyrins have been widely investigated as functional materials for chemical sensor fabrication due to their several unique and interesting physico-chemical properties. Structural differences between free-base and metal substituted porphyrins make them suitable for improving selectivity of sensors. However, their poor conductivity is an impediment in fabrication of prophyrin-based chemiresistor sensors. The present attempt is to resolve these issues by combining freebase- and metallo-porphyrins with SWNTs to fabricate SWNTs-porphyrin hybrid chemiresistor sensor arrays for monitoring volatile organic carbons (VOCs) in air. Differences in sensing performance were noticed for porphyrin with different functional group and with different central metal atom. The mechanistic study for acetone sensing was done using field-effect transistor (FET) measurements and revealed that the sensing mechanism of ruthenium octaethyl porphyrin hybrid device was governed by electrostatic gating effect, whereas iron tetraphenyl porphyrin hybrid device was governed by electrostatic gating and Schottky barrier modulation in combination. Further, the recorded electronic responses for all hybrid sensors were analyzed using a pattern-recognition analysis tool. The pattern-recognition analysis confirmed a definite pattern in response for different hybrid material and could efficiently differentiate analytes from one another. This discriminating capability of the hybrid nanosensor devices open up the possibilities for further development of highly dense nanosensor array with suitable porphyrin for E-nose application.

Dataset Information

Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.

Publications

Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: highly versatile building blocks for self-assembly of polymers and discrete arrays.

Similar Datasets

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