Synthesis of C60-diphenylaminofluorene dyads with two-photon absorbing characteristics

Prashant A. Padmawar; Taizoon Canteenwala; Sarika Verma; Loon Seng Tan; Guang S. He; Paras N. Prasad; Long Y. Chiang

doi:10.1016/j.synthmet.2005.07.047

Synthesis of C₆₀-diphenylaminofluorene dyads with two-photon absorbing characteristics

Prashant A. Padmawar
, Taizoon Canteenwala
, Sarika Verma
, Loon Seng Tan
, Guang S. He
, Paras N. Prasad
, Long Y. Chiang

Chemistry

University at Buffalo

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

14 Scopus citations

Abstract

Linear A-sp³-D molecular conjugates as 9,9-dialkyl-2-diphenylaminofluorene (DPAF-C,)-C₆₀ monoadducts were demonstrated using methanoketo unit as a linker to bridge the DPAF donor moiety and the fullerene acceptor chromophore together within a short distance of roughly 2.0 Å. Target products of C₆₀-diphenylaminofluorene dyads C₆₀(>DPAF-C₂) and C₆₀(>DPAF-C ₁₈) were synthesized using Bingel cycloproanation reaction from the corresponding 7-α-bromoacetyl-9,9-dialkyl-2-diphenylaminofluorene precursors. Both dyads C₆₀(>DPAF-C₂) and C ₆₀(>DPAF-C₁₈) were characterized by spectroscopic methods and simultaneous two-photon excitation measurements, showing large two-photon absorption cross-sections in the nanosecond regime.

Original language	English
Pages (from-to)	185-188
Number of pages	4
Journal	Synthetic Metals
Volume	154
Issue number	1-3
DOIs	https://doi.org/10.1016/j.synthmet.2005.07.047
State	Published - Sep 22 2005

Keywords

Diphenylaminofluorene
Donor-acceptor conjugate
Fullerene derivative
Photonic organics
Two-photon absorption

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10.1016/j.synthmet.2005.07.047

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@article{b7827214b5c8437593998a6deb4a1a7c,

title = "Synthesis of C60-diphenylaminofluorene dyads with two-photon absorbing characteristics",

abstract = "Linear A-sp3-D molecular conjugates as 9,9-dialkyl-2-diphenylaminofluorene (DPAF-C,)-C60 monoadducts were demonstrated using methanoketo unit as a linker to bridge the DPAF donor moiety and the fullerene acceptor chromophore together within a short distance of roughly 2.0 {\AA}. Target products of C60-diphenylaminofluorene dyads C60(>DPAF-C2) and C60(>DPAF-C 18) were synthesized using Bingel cycloproanation reaction from the corresponding 7-α-bromoacetyl-9,9-dialkyl-2-diphenylaminofluorene precursors. Both dyads C60(>DPAF-C2) and C 60(>DPAF-C18) were characterized by spectroscopic methods and simultaneous two-photon excitation measurements, showing large two-photon absorption cross-sections in the nanosecond regime.",

keywords = "Diphenylaminofluorene, Donor-acceptor conjugate, Fullerene derivative, Photonic organics, Two-photon absorption",

author = "Padmawar, \{Prashant A.\} and Taizoon Canteenwala and Sarika Verma and Tan, \{Loon Seng\} and He, \{Guang S.\} and Prasad, \{Paras N.\} and Chiang, \{Long Y.\}",

year = "2005",

month = sep,

day = "22",

doi = "10.1016/j.synthmet.2005.07.047",

language = "English",

volume = "154",

pages = "185--188",

journal = "Synthetic Metals",

issn = "0379-6779",

publisher = "Elsevier B.V.",

number = "1-3",

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TY - JOUR

T1 - Synthesis of C60-diphenylaminofluorene dyads with two-photon absorbing characteristics

AU - Padmawar, Prashant A.

AU - Canteenwala, Taizoon

AU - Verma, Sarika

AU - Tan, Loon Seng

AU - He, Guang S.

AU - Prasad, Paras N.

AU - Chiang, Long Y.

PY - 2005/9/22

Y1 - 2005/9/22

N2 - Linear A-sp3-D molecular conjugates as 9,9-dialkyl-2-diphenylaminofluorene (DPAF-C,)-C60 monoadducts were demonstrated using methanoketo unit as a linker to bridge the DPAF donor moiety and the fullerene acceptor chromophore together within a short distance of roughly 2.0 Å. Target products of C60-diphenylaminofluorene dyads C60(>DPAF-C2) and C60(>DPAF-C 18) were synthesized using Bingel cycloproanation reaction from the corresponding 7-α-bromoacetyl-9,9-dialkyl-2-diphenylaminofluorene precursors. Both dyads C60(>DPAF-C2) and C 60(>DPAF-C18) were characterized by spectroscopic methods and simultaneous two-photon excitation measurements, showing large two-photon absorption cross-sections in the nanosecond regime.

AB - Linear A-sp3-D molecular conjugates as 9,9-dialkyl-2-diphenylaminofluorene (DPAF-C,)-C60 monoadducts were demonstrated using methanoketo unit as a linker to bridge the DPAF donor moiety and the fullerene acceptor chromophore together within a short distance of roughly 2.0 Å. Target products of C60-diphenylaminofluorene dyads C60(>DPAF-C2) and C60(>DPAF-C 18) were synthesized using Bingel cycloproanation reaction from the corresponding 7-α-bromoacetyl-9,9-dialkyl-2-diphenylaminofluorene precursors. Both dyads C60(>DPAF-C2) and C 60(>DPAF-C18) were characterized by spectroscopic methods and simultaneous two-photon excitation measurements, showing large two-photon absorption cross-sections in the nanosecond regime.

KW - Diphenylaminofluorene

KW - Donor-acceptor conjugate

KW - Fullerene derivative

KW - Photonic organics

KW - Two-photon absorption

UR - https://www.scopus.com/pages/publications/24644524185

U2 - 10.1016/j.synthmet.2005.07.047

DO - 10.1016/j.synthmet.2005.07.047

M3 - Article

SN - 0379-6779

VL - 154

SP - 185

EP - 188

JO - Synthetic Metals

JF - Synthetic Metals

IS - 1-3

ER -

Synthesis of C₆₀-diphenylaminofluorene dyads with two-photon absorbing characteristics

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Keywords

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