Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

Eric Mertz; Stephanie L. Elmer; Amy M. Balija; Steven C. Zimmerman

doi:10.1016/j.tet.2004.08.100

Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

Eric Mertz, Stephanie L. Elmer, Amy M. Balija, Steven C. Zimmerman

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting. Graphical Abstract.

Original language	English
Pages (from-to)	11191-11204
Number of pages	14
Journal	Tetrahedron
Volume	60
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2004.08.100
State	Published - 29 Nov 2004
Externally published	Yes

Keywords

Chemosensor
Dendritic host
Diamines

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2004.08.100

Cite this

@article{d66d6ab6a1af47fcba345917749b1fa8,

title = "Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts",

abstract = "Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting. Graphical Abstract.",

keywords = "Chemosensor, Dendritic host, Diamines",

author = "Eric Mertz and Elmer, {Stephanie L.} and Balija, {Amy M.} and Zimmerman, {Steven C.}",

note = "Funding Information: Funding of this work by the National Institutes of Health (GM61067) is gratefully acknowledged. The authors thank Melissa J. Witmer for early work on the X-ray analysis and James B. Beil, Annabelle Benin, Brian G. Carter, and Denise M. Junge for assistance with preparative work. ",

year = "2004",

month = nov,

day = "29",

doi = "10.1016/j.tet.2004.08.100",

language = "English",

volume = "60",

pages = "11191--11204",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "49",

}

TY - JOUR

T1 - Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

AU - Mertz, Eric

AU - Elmer, Stephanie L.

AU - Balija, Amy M.

AU - Zimmerman, Steven C.

N1 - Funding Information: Funding of this work by the National Institutes of Health (GM61067) is gratefully acknowledged. The authors thank Melissa J. Witmer for early work on the X-ray analysis and James B. Beil, Annabelle Benin, Brian G. Carter, and Denise M. Junge for assistance with preparative work.

PY - 2004/11/29

Y1 - 2004/11/29

N2 - Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting. Graphical Abstract.

AB - Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting. Graphical Abstract.

KW - Chemosensor

KW - Dendritic host

KW - Diamines

UR - http://www.scopus.com/inward/record.url?scp=7044229864&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.08.100

DO - 10.1016/j.tet.2004.08.100

M3 - Article

AN - SCOPUS:7044229864

SN - 0040-4020

VL - 60

SP - 11191

EP - 11204

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this