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새로운 잠재지문 현출제로서 Fluoran leuco 염료의 할로변색 반응에 근거한 Cyclic Nitronate 분자의 설계와 정량적인 구조-성질관계

A Molecular Design of Cyclic Nitronate Dye Based on the Halochromism of Fluoran Leuco Dyes as a New Latent Fingerprint Development Agent and Quantitative Structure-Property Relationships

최미정|성낙도|전우현
한국과학수사학회 (The Korean Academy of Scientific Criminal Investigation)|2022.03|과학수사학회지 (Journal of Science Criminal Investigation)|제16권 제1호|pp. 9-19|DOI 10.20297/jsci.2022.16.1.9

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참고문헌

키워드

DFTFluoran leuco dyeNew anti-Stokes fingerprinting powder (C)FMO energy2D-QSPRs

초록

새로운 잠재지문 현출제로서 fluoran leuco dye의 할로변색 반응에 근거하여 Me too approach 방법에 따라 cyclic nitronate (A 및 C) 분자를 설계하였다. 그리고 염료 분자들의 경계분자궤도(FMO) 에너지(ev.)를 밀도범함수론(DFT)으로 계산하고 2차원적인 정량적 구조와 성질과의 관계(2D-QSPRs)를 검토하였다. 그 결과로부터, 형광 양자수율(Φ)은 주로 전자끌게(Σσ>0; ρ > δ) 그리고 소수성(logP>0)은 입체적으로 큰 치환기(R1-R3) 효과(ΣEs<0; δ > ρ)에 의하여 증가하였다. 또한, 분자간 FMO 에너지 차이(ΔE) 의 비교로부터, C 분자에 대한 반응성은 친수성 아미노산(P)이 소수성 지방산(F)보다 큰 경향(P>F)이었다. 그러므로 C 분자는 잠재지문 현출반응의 조건에 따라 양자성 용매(logP<0)에서는 아미노산, 그리고 비양자성(logP>0) 또는 분말 조건(감열지)에서는 지방산을 대상으로 하는 두 가지 잠재지문 현출용도로 적합할 것이라 예상되었다

Abstract

The cyclic nitronate (A & C) molecules basis on the halochromism reaction of fluoran leuco dyes as a new latent fingerprints development agent were designed according to structure based Me too approach method. And the FMO (frontier molecular orbital) energies (ev.) of the dye molecules were calculated by density functional theory (DFT), and 2 dimensional quantitative structure-property relationships (2D-QSPRs) were reviewed quantitatively. From the results, fluorescence quantum yield (Φ) was mainly increased by electron withdrawing groups (Σσ>0; ρ>δ), and hydrophobicity (logP>0) was increased by steric effect (ΣEs<0; δ>ρ) with large substituents (R1-R3). Furthermore, from the comparison of intermolecular FMO energy differences (ΔE), reactivity to the C molecule tended to be more hydrophilic amino acids (P) than hydrophobic fatty acids (F). Therefore, it was predicted that the C molecules would be suitable for the two latent fingerprints development reactions for amino acids in protic solvents (logP<0) and fatty acids in aprotic solvents (logP>0) or powder conditions (thermal paper), depending on the conditions of the latent fingerprinting reaction.

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