Frustration of condensed phase aggregation of naphthalocyanine by dendritic site-isolation

Xiaochun Chen, Nilmi Fernando, Dominic V Mcgrath

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The synthesis and aggregation studies of a pair of 3, 4,12,13,21,22,30,31- octasubstituted 2,3-Naphthalocyanine (Ncs) 1 and 2 was reported. The synthetic route leading to these naphthalonitriles started from dimethyl 4,5-dihydroxyphthalate onto which the previously synthesized dendritic alcohols 3 and 4 were introduced through the Mitsunobu protocol. The obtained diesters 6 and 7 were reduced to the corresponding 1,2-dimethanols (8 and 9), and subsequent Swern oxidation provided the disubstituted dendritic phthalaldehydes 10 and 11. Finally, 10 and 11 were converted to naphthalonitriles 12 and 13 through base-promoted condensation with succinonitrile in DMSO. Compounds 1 and 2 were purified by flash column chromatography. Initial molecular aggregation studies were performed in solution as a function of increasing volume fraction of EtOH. The B-bands at 332 and 402 nm exhibited only slight hypochromicity during this change in solvent conditions.

Original languageEnglish (US)
Pages (from-to)5512-5514
Number of pages3
JournalMacromolecules
Volume43
Issue number13
DOIs
StatePublished - Jul 13 2010

Fingerprint

Agglomeration
Column chromatography
Dimethyl Sulfoxide
Condensation
Volume fraction
Alcohols
Oxidation
succinonitrile
2,3-naphthalocyanine

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

Frustration of condensed phase aggregation of naphthalocyanine by dendritic site-isolation. / Chen, Xiaochun; Fernando, Nilmi; Mcgrath, Dominic V.

In: Macromolecules, Vol. 43, No. 13, 13.07.2010, p. 5512-5514.

Research output: Contribution to journalArticle

@article{fcfe091416b843c9b5a73bf463ff223d,
title = "Frustration of condensed phase aggregation of naphthalocyanine by dendritic site-isolation",
abstract = "The synthesis and aggregation studies of a pair of 3, 4,12,13,21,22,30,31- octasubstituted 2,3-Naphthalocyanine (Ncs) 1 and 2 was reported. The synthetic route leading to these naphthalonitriles started from dimethyl 4,5-dihydroxyphthalate onto which the previously synthesized dendritic alcohols 3 and 4 were introduced through the Mitsunobu protocol. The obtained diesters 6 and 7 were reduced to the corresponding 1,2-dimethanols (8 and 9), and subsequent Swern oxidation provided the disubstituted dendritic phthalaldehydes 10 and 11. Finally, 10 and 11 were converted to naphthalonitriles 12 and 13 through base-promoted condensation with succinonitrile in DMSO. Compounds 1 and 2 were purified by flash column chromatography. Initial molecular aggregation studies were performed in solution as a function of increasing volume fraction of EtOH. The B-bands at 332 and 402 nm exhibited only slight hypochromicity during this change in solvent conditions.",
author = "Xiaochun Chen and Nilmi Fernando and Mcgrath, {Dominic V}",
year = "2010",
month = "7",
day = "13",
doi = "10.1021/ma100902m",
language = "English (US)",
volume = "43",
pages = "5512--5514",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "13",

}

TY - JOUR

T1 - Frustration of condensed phase aggregation of naphthalocyanine by dendritic site-isolation

AU - Chen, Xiaochun

AU - Fernando, Nilmi

AU - Mcgrath, Dominic V

PY - 2010/7/13

Y1 - 2010/7/13

N2 - The synthesis and aggregation studies of a pair of 3, 4,12,13,21,22,30,31- octasubstituted 2,3-Naphthalocyanine (Ncs) 1 and 2 was reported. The synthetic route leading to these naphthalonitriles started from dimethyl 4,5-dihydroxyphthalate onto which the previously synthesized dendritic alcohols 3 and 4 were introduced through the Mitsunobu protocol. The obtained diesters 6 and 7 were reduced to the corresponding 1,2-dimethanols (8 and 9), and subsequent Swern oxidation provided the disubstituted dendritic phthalaldehydes 10 and 11. Finally, 10 and 11 were converted to naphthalonitriles 12 and 13 through base-promoted condensation with succinonitrile in DMSO. Compounds 1 and 2 were purified by flash column chromatography. Initial molecular aggregation studies were performed in solution as a function of increasing volume fraction of EtOH. The B-bands at 332 and 402 nm exhibited only slight hypochromicity during this change in solvent conditions.

AB - The synthesis and aggregation studies of a pair of 3, 4,12,13,21,22,30,31- octasubstituted 2,3-Naphthalocyanine (Ncs) 1 and 2 was reported. The synthetic route leading to these naphthalonitriles started from dimethyl 4,5-dihydroxyphthalate onto which the previously synthesized dendritic alcohols 3 and 4 were introduced through the Mitsunobu protocol. The obtained diesters 6 and 7 were reduced to the corresponding 1,2-dimethanols (8 and 9), and subsequent Swern oxidation provided the disubstituted dendritic phthalaldehydes 10 and 11. Finally, 10 and 11 were converted to naphthalonitriles 12 and 13 through base-promoted condensation with succinonitrile in DMSO. Compounds 1 and 2 were purified by flash column chromatography. Initial molecular aggregation studies were performed in solution as a function of increasing volume fraction of EtOH. The B-bands at 332 and 402 nm exhibited only slight hypochromicity during this change in solvent conditions.

UR - http://www.scopus.com/inward/record.url?scp=77955834032&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955834032&partnerID=8YFLogxK

U2 - 10.1021/ma100902m

DO - 10.1021/ma100902m

M3 - Article

AN - SCOPUS:77955834032

VL - 43

SP - 5512

EP - 5514

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 13

ER -