Synthesis, characterization, and optical properties of new two-photon-absorbing fluorene derivatives

Kevin D. Belfield; Alma R. Morales; Bong Soo Kang; Joel M. Hales; David J. Hagan; Eric W. Van Stryland; Victor M. Chapela; Judith Percino

doi:10.1021/cm049872g

Synthesis, characterization, and optical properties of new two-photon-absorbing fluorene derivatives

Kevin D. Belfield, Alma R. Morales, Bong Soo Kang, Joel M. Hales, David J. Hagan, Eric W. Van Stryland, Victor M. Chapela, Judith Percino

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147 Scopus citations

Abstract

The synthesis of a series of four new compounds containing fluorenyl chromophores is presented, along with the results of spectroscopic and photochemical studies aimed at understanding the two-photon absorption properties and energetics of their electronically excited states. The molecular structures of the compounds were systematically varied to allow comparison of molecules possessing high and low molecular symmetry, short and long alkyl chains, and a fluorenyl conjugated π-system. Solvent-dependent absorption and emission were investigated along with π-conjugation length. Preliminary measurements of two-photon absorption (2PA) using a two-photon fluorescence method indicate that these chromophores exhibit high two-photon absorptivity. A symmetrical molecule (3), possessing a relatively large π-conjugated system, flanked on either side by electron-withdrawing groups (benzothiazole), exhibited a peak 2PA cross section (δ) of 6000 × 10^-50 cm ⁴ s photon^-1 molecule^-1 at 600 nm. Excitation anisotropy studies revealed the position of the S₀ → S ₁ and S₀ → S₂ electronic transitions. Consistent with quantum mechanical selection rules, the two-photon allowed transition (S₀ → S₂) was dominant.

Original language	English (US)
Pages (from-to)	4634-4641
Number of pages	8
Journal	Chemistry of Materials
Volume	16
Issue number	23
DOIs	https://doi.org/10.1021/cm049872g
State	Published - Nov 16 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering
Materials Chemistry

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title = "Synthesis, characterization, and optical properties of new two-photon-absorbing fluorene derivatives",

abstract = "The synthesis of a series of four new compounds containing fluorenyl chromophores is presented, along with the results of spectroscopic and photochemical studies aimed at understanding the two-photon absorption properties and energetics of their electronically excited states. The molecular structures of the compounds were systematically varied to allow comparison of molecules possessing high and low molecular symmetry, short and long alkyl chains, and a fluorenyl conjugated π-system. Solvent-dependent absorption and emission were investigated along with π-conjugation length. Preliminary measurements of two-photon absorption (2PA) using a two-photon fluorescence method indicate that these chromophores exhibit high two-photon absorptivity. A symmetrical molecule (3), possessing a relatively large π-conjugated system, flanked on either side by electron-withdrawing groups (benzothiazole), exhibited a peak 2PA cross section (δ) of 6000 × 10-50 cm 4 s photon-1 molecule-1 at 600 nm. Excitation anisotropy studies revealed the position of the S0 → S 1 and S0 → S2 electronic transitions. Consistent with quantum mechanical selection rules, the two-photon allowed transition (S0 → S2) was dominant.",

author = "Belfield, {Kevin D.} and Morales, {Alma R.} and Kang, {Bong Soo} and Hales, {Joel M.} and Hagan, {David J.} and {Van Stryland}, {Eric W.} and Chapela, {Victor M.} and Judith Percino",

year = "2004",

month = nov,

day = "16",

doi = "10.1021/cm049872g",

language = "English (US)",

volume = "16",

pages = "4634--4641",

journal = "Chemistry of Materials",

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T1 - Synthesis, characterization, and optical properties of new two-photon-absorbing fluorene derivatives

AU - Belfield, Kevin D.

AU - Morales, Alma R.

AU - Kang, Bong Soo

AU - Hales, Joel M.

AU - Hagan, David J.

AU - Van Stryland, Eric W.

AU - Chapela, Victor M.

AU - Percino, Judith

PY - 2004/11/16

Y1 - 2004/11/16

N2 - The synthesis of a series of four new compounds containing fluorenyl chromophores is presented, along with the results of spectroscopic and photochemical studies aimed at understanding the two-photon absorption properties and energetics of their electronically excited states. The molecular structures of the compounds were systematically varied to allow comparison of molecules possessing high and low molecular symmetry, short and long alkyl chains, and a fluorenyl conjugated π-system. Solvent-dependent absorption and emission were investigated along with π-conjugation length. Preliminary measurements of two-photon absorption (2PA) using a two-photon fluorescence method indicate that these chromophores exhibit high two-photon absorptivity. A symmetrical molecule (3), possessing a relatively large π-conjugated system, flanked on either side by electron-withdrawing groups (benzothiazole), exhibited a peak 2PA cross section (δ) of 6000 × 10-50 cm 4 s photon-1 molecule-1 at 600 nm. Excitation anisotropy studies revealed the position of the S0 → S 1 and S0 → S2 electronic transitions. Consistent with quantum mechanical selection rules, the two-photon allowed transition (S0 → S2) was dominant.

AB - The synthesis of a series of four new compounds containing fluorenyl chromophores is presented, along with the results of spectroscopic and photochemical studies aimed at understanding the two-photon absorption properties and energetics of their electronically excited states. The molecular structures of the compounds were systematically varied to allow comparison of molecules possessing high and low molecular symmetry, short and long alkyl chains, and a fluorenyl conjugated π-system. Solvent-dependent absorption and emission were investigated along with π-conjugation length. Preliminary measurements of two-photon absorption (2PA) using a two-photon fluorescence method indicate that these chromophores exhibit high two-photon absorptivity. A symmetrical molecule (3), possessing a relatively large π-conjugated system, flanked on either side by electron-withdrawing groups (benzothiazole), exhibited a peak 2PA cross section (δ) of 6000 × 10-50 cm 4 s photon-1 molecule-1 at 600 nm. Excitation anisotropy studies revealed the position of the S0 → S 1 and S0 → S2 electronic transitions. Consistent with quantum mechanical selection rules, the two-photon allowed transition (S0 → S2) was dominant.

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DO - 10.1021/cm049872g

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JO - Chemistry of Materials

JF - Chemistry of Materials

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Synthesis, characterization, and optical properties of new two-photon-absorbing fluorene derivatives

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