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Glad to share with you that we had found below as an answer, in general, that
$$\boxed{ \int_0^{\frac\pi2} {\sin^n x} \ln{(\tan x)} \,dx =\frac{\sqrt{\pi}}{4 \Gamma\left(\frac{n}{2}+1\right)} \Gamma\left(\frac{n+1}{2}\right) \left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right]}$$ where $n\in \mathbb N$.
After reading the post with the result $$\int_0^{\frac\pi2} {\sin^2{x} \ln{(\tan x)} \,dx}=\frac{\pi}{4}$$ I was attracted by its decency and wanted to generalise it as $$ I_n=\int_0^{\frac{\pi}{2}} \sin ^{2 n} x \ln (\tan x) d x \stackrel{x\mapsto\frac \pi 2- x}{=}- \int_0^{\frac{\pi}{2}} \cos ^{2 n} x \ln (\tan x) d x =-J_n, $$ For convenience, I started with the second integral,
$$ J_n=\int_0^{\frac{\pi}{2}} \cos ^{2 n} x \ln (\tan x) d x, $$
Letting $u=\tan x$ transforms the integral into $$ J_n=\int_0^{\infty} \frac{\ln u}{\left(1+u^2\right)^{n+1}} d u $$ Differentiating the following famous result w.r.t. $a$ by $n$ times $$ K(a)=\int_0^{\infty} \frac{\ln u}{a+u^2} d u=\frac{\pi \ln a}{4 \sqrt{a}}, (\textrm{ for }a>0) $$
(refer post for details)
yields $$ \begin{aligned}J_n&=\left.\frac{(-1)^n}{n !} \frac{\partial^n K(a)}{\partial a^n}\right|_{a=1}\\&=\left.\frac{(-1)^n \pi}{4n !} \frac{\partial^n}{\partial a^n}\left(\frac{\ln a}{\sqrt{a}}\right)\right|_{a=1} \\&=\frac{\pi}{4 n !}\left(\frac{1}{2}\right)_n\left[\psi\left(\frac{1}{2}\right)-\psi\left(\frac{1}{2}-n\right)\right] \cdots (*)\end{aligned} $$ We can now conclude that
$$\boxed{J_n= \frac{\pi(2 n) !}{4^{n+1}(n !)^2}\left[\psi\left(\frac{1}{2}\right)-\psi\left(\frac{1}{2}-n\right)\right]=-I_n}$$
For examples, $$ J_1=-\frac{\pi}{4} ; \quad J_2=-\frac{\pi}{4}; \quad J_3=-\frac{23 \pi}{96}; \quad J_4=-\frac{11\pi}{48} ; \quad J_5=-\frac{563\pi}{2560} ; \quad J_6=-\frac{1627\pi}{7680};\cdots $$ and $$ I_1=\frac{\pi}{4} ; \quad I_2=\frac{\pi}{4}; \quad I_3=\frac{23 \pi}{96}; \quad I_4=\frac{11\pi}{48} ; \quad I_5=\frac{563\pi}{2560} ; \quad I_6=\frac{1627\pi}{7680};\cdots $$
My questions:
- Any other alternative method of evaluating $\int_0^{\frac{\pi}{2}} \sin ^{2 n} x \ln (\tan x) d x $?
- Can the result (*) found in Wolframalpha be proved?
Inspired by Miracle Invoker, I had just found the exact value of
$$\boxed{A_n= \int_0^{\frac\pi2} {\sin^n x} \ln{(\tan x)} \,dx =\frac{\sqrt{\pi}}{4 \Gamma\left(\frac{n}{2}+1\right)} \Gamma\left(\frac{n+1}{2}\right) \left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right]}$$ and $$\boxed{ B_n=\int_0^{\frac\pi2} {\cos^n x} \ln{(\tan x)} \,dx =-\frac{\sqrt{\pi}}{4 \Gamma\left(\frac{n}{2}+1\right)} \Gamma\left(\frac{n+1}{2}\right) \left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right]}$$
where $n\in \mathbb N.$
Noticing that
$$ A_n=\left.\frac{\partial}{\partial a}\left(A_n(a)\right)\right|_{a=0} $$
where \begin{aligned}A_n (a) & =\int_0^{\frac{\pi}{2}} \sin ^{n} x \tan ^a x d x \\ & =\int_0^{\frac{\pi}{2}} \sin ^{n+a} x \cos ^{-a} x d x \\ & =\frac{1}{2} B\left(\frac{n+a+1}{2}, \frac{1-a}{2}\right) \\ & =\frac{1}{2 \Gamma(\frac n2+1) } \Gamma\left(\frac{n+a+1}{2}\right) \Gamma\left(\frac{1-a}{2}\right) \end{aligned} Using logarithmic differentiation, we have $$ \frac{A_n^{\prime}(a)}{A_n(a)}=\frac{1}{2}\left[\psi\left(\frac{n+a+1}{2}\right)-\psi\left(\frac{1-a}{2}\right)\right] $$ Setting $a=0$ yields $$ \begin{aligned} A_n^{\prime}(0) & =\frac{1}{2} A_n(0)\left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right] \\ & =\frac{1}{2} \cdot \frac{1}{2\Gamma(\frac n2+1 )} \Gamma\left(\frac{n+1}{2}\right) \Gamma\left(\frac{1}{2}\right)\left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right]\\ \end{aligned} $$ We can now conclude that $$\boxed{ \int_0^{\frac\pi2} {\sin^n x} \ln{(\tan x)} \,dx =\frac{\sqrt{\pi}}{4 \Gamma\left(\frac{n}{2}+1\right)} \Gamma\left(\frac{n+1}{2}\right) \left[\psi\left(\frac{n+1}{2}\right)-\psi\left(\frac{1}{2}\right)\right]=-B_n}$$
For examples,
$$ \left\{A_n\right\}_{n=1}^{10}= \left\{\log 2, \frac{\pi}{4}, \frac{1}{3}(1+2\log 2), \frac{\pi}{4}, \frac{2}{15}(3+4\log 2), \frac{23 \pi}{96},\\ \qquad\qquad \qquad\qquad \frac{4}{105}(11+12\log 2), \frac{11 \pi}{48}, \frac{16}{945}(25+24\log 2), \frac{563 \pi}{2560}\right\} $$
and $$ \left\{B_n\right\}_{n=1}^{10}= \left\{-\log 2, -\frac{\pi}{4}, -\frac{1}{3}(1+2\log 2), -\frac{\pi}{4}, -\frac{2}{15}(3+4\log 2), -\frac{23 \pi}{96},\\ \qquad\qquad \qquad\qquad - \frac{4}{105}(11+12\log 2), -\frac{11 \pi}{48}, -\frac{16}{945}(25+24\log 2), -\frac{563 \pi}{2560}\right\} $$